Organic Letters (ACS Publications) - American Chemical Society [PDF]

Oct 1, 2010 - Sen W. Kwok, Joseph R. Fotsing, Rebecca J. Fraser, Valentin O. Rodionov, and Valery V. Fokin. pp 4217–42

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Table of Contents October 1, 2010 Volume 12, Issue 19 Pages 4217-4434

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LETTERS

Transition-Metal-Free Catalytic Synthesis of 1,5-Diaryl-1,2,3-triazoles

Abstract | Supporting Info

Sen W. Kwok, Joseph R. Fotsing, Rebecca J. Fraser, Valentin O. Rodionov, and Valery V. Fokin pp 4217–4219 Publication Date (Web): September 8, 2010 (Letter) DOI: 10.1021/ol101568d

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Acetoacetanilides as Masked Isocyanates: Facile and Efficient Synthesis of Unsymmetrically Substituted Ureas

Abstract | Supporting Info

Ying Wei, Jing Liu, Shaoxia Lin, Hongqian Ding, Fushun Liang, and Baozhong Zhao pp 4220–4223 Publication Date (Web): September 1, 2010 (Letter) DOI: 10.1021/ol101474f

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Figure 1 of 3

Total Synthesis of Rhazinilam: Axial to Point Chirality Transfer in an Enantiospecific PdCatalyzed Transannular Cyclization

Abstract | Supporting Info

Zhenhua Gu and Armen Zakarian pp 4224–4227 Publication Date (Web): August 26, 2010 (Letter) DOI: 10.1021/ol101523z

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C3-Symmetric Cage-like Receptors: Chiral Discrimination of -Chiral Amines in a Confined Space Sunderraman Sambasivan, Sung-Gon Kim, Sun Mi Choi, Young Min Rhee, and Kyo Han Ahn pp 4228–4231 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol1015527

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Imidazole-Catalyzed Monoacylation of Symmetrical Diamines

Abstract | Supporting Info

Sanjeev K. Verma, B. N. Acharya, and M. P. Kaushik pp 4232–4235 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101604q

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Phenylene Bridged Boron−Nitrogen Containing Dendrimers

Abstract | Supporting Info

Agnieszka Proń, Martin Baumgarten, and Klaus Müllen pp 4236–4239 Publication Date (Web): September 7, 2010 (Letter) DOI: 10.1021/ol101327h

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Copper-Catalyzed Synthesis of -Amino Imides from Tertiary Amines: Ugi-Type ThreeComponent Assemblies Involving Direct Functionalization of sp3 C−Hs Adjacent to Nitrogen Atoms Xin Ye, Chunsong Xie, Yuanyuan Pan, Laihong Han, and Tian Xie pp 4240–4243 Publication Date (Web): September 9, 2010 (Letter) DOI: 10.1021/ol101576q

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Ring Opening of a Trisubstituted Aziridine With Amines: Regio- and Stereoselective Formation of Substituted 1,2-Diamines

Abstract | Supporting Info

Brandon T. Kelley and Madeleine M. Joullié pp 4244–4247 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101584z

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A New [3]Rotaxane Molecular Machine Based on a Dibenzylammonium Ion and a Triazolium Station Yi Jiang, Jia-Bin Guo, and Chuan-Feng Chen pp 4248–4251 Publication Date (Web): September 9, 2010 (Letter) DOI: 10.1021/ol101920b

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Biotransformation of Cycloastragenol by Cunninghamella blakesleeana NRRL 1369 Resulting in a Novel Framework Melis Kuban, Gaye Öngen, and Erdal Bedir pp 4252–4255 Publication Date (Web): September 1, 2010 (Letter) DOI: 10.1021/ol101642a

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“Click” Reaction in Conjunction with Diazeniumdiolate Chemistry: Developing High-Load Nitric Oxide Donors Oyebola A. Oladeinde, Sam Y. Hong, Ryan J. Holland, Anna E. Maciag, Larry K. Keefer, Joseph E. Saavedra, and Rahul S. Nandurdikar pp 4256–4259 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101645k

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Organocatalytic and Electrophilic Approach to Oxindoles with C3-Quaternary Stereocenters Jing Peng, Xin Huang, Hai-Lei Cui, and Ying-Chun Chen pp 4260–4263 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101668z

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Helical and Flat Structures from Chiral Dendronized Rectangular Oligo(phenylene ethynylene)s

Abstract | Supporting Info

Fátima García, Fátima Aparicio, Marco Marenchino, Ramón Campos-Olivas, and Luis Sánchez pp 4264–4267 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101673z

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Diastereoselective Conjugate Addition of Organocuprates to Chiral N-Enoyl Oxazolidinethiones

Abstract | Supporting Info

Rocío Sabala, Luis Hernández-García, Aurelio Ortiz, Moisés Romero, and Horacio F. Olivo pp 4268–4270 Publication Date (Web): August 31, 2010 (Letter) DOI: 10.1021/ol101687e

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A Stereocontrolled Synthesis of (±)-Xenovenine via a Scandium(III)-Catalyzed Internal Aminodiene Bicyclization Terminated by a 2-(5-Ethyl-2-thienyl)ethenyl Group

Abstract | Supporting Info

Tao Jiang and Tom Livinghouse pp 4271–4273 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101646t

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Rhenium-Catalyzed Diastereoselective Synthesis of Aminoindanes via the Insertion of Allenes into a C−H Bond

Abstract | Supporting Info

Yoichiro Kuninobu, Peng Yu, and Kazuhiko Takai pp 4274–4276 Publication Date (Web): August 30, 2010 (Letter) DOI: 10.1021/ol101627x

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Iron-Catalyzed Heterocycle and Arene Deprotonative Alkylation

Abstract | Supporting Info

Ly Dieu Tran and Olafs Daugulis pp 4277–4279 Publication Date (Web): September 8, 2010 (Letter) DOI: 10.1021/ol101684u

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Molybdenum-Mediated Carbonylation of Aryl Halides with Nucleophiles Using Microwave Irradiation Bryan Roberts, David Liptrot, Lilian Alcaraz, Tim Luker, and Michael J. Stocks pp 4280–4283 Publication Date (Web): August 26, 2010 (Letter) DOI: 10.1021/ol1016965

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A Biomimetic Total Synthesis of (+)-Ainsliadimer A

Abstract | Supporting Info

Chao Li, Xueliang Yu, and Xiaoguang Lei pp 4284–4287 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101705j

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Synthesis of Highly Fluorinated 2,2¢ -Biphenols and 2,2¢ -Bisanisoles

Abstract | Supporting Info

Robert Francke, Gregor Schnakenburg, and Siegfried R. Waldvogel pp 4288–4291 Publication Date (Web): August 30, 2010 (Letter) DOI: 10.1021/ol101698a

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Monanchocidin: A New Apoptosis-Inducing Polycyclic Guanidine Alkaloid from the Marine Sponge Monanchora pulchra Alla G. Guzii, Tatyana N. Makarieva, Vladimir A. Denisenko, Pavel S. Dmitrenok, Alexandra S. Kuzmich, Sergey A. Dyshlovoy, Vladimir B. Krasokhin, and Valentin A. Stonik pp 4292–4295 Publication Date (Web): August 30, 2010 (Letter) DOI: 10.1021/ol101716x

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Catalytic Asymmetric Synthesis of Quaternary -Hydroxy Trifluoromethyl Phosphonate via Chiral Aluminum(III) Catalyzed Hydrophosphonylation of Trifluoromethyl Ketones Xin Zhou, Qi Zhang, Yonghai Hui, Weiliang Chen, Jun Jiang, Lili Lin, Xiaohua Liu, and Xiaoming Feng pp 4296–4299 Publication Date (Web): September 1, 2010 (Letter) DOI: 10.1021/ol101737b

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Synthesis of Inherently Chiral Azacalix[4]arenes and Diazadioxacalix[4]arenes

Abstract | Supporting Info

Jeffrey L. Katz and Brittany A. Tschaen pp 4300–4303 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol1017454

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Pericyclic Reaction of a Zwitterionic Salt of an Enedione-diazoester. A Novel Strategy for the Synthesis of Highly Functionalized Resorcinols Yu Liu, Kanwarpal Bakshi, Peter Zavalij, and Michael P. Doyle pp 4304–4307 Publication Date (Web): September 1, 2010 (Letter) DOI: 10.1021/ol101744h

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Total Synthesis and Biological Evaluation of Tyroscherin

Abstract | Supporting Info

Hyun Seop Tae, John Hines, Ashley R. Schneekloth, and Craig M. Crews pp 4308–4311 Publication Date (Web): September 10, 2010 (Letter) DOI: 10.1021/ol101801u

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Selective Acetylation of per-O-TMS-Protected Monosaccharides

Abstract | Supporting Info

Mark A. Witschi and Jacquelyn Gervay-Hague pp 4312–4315 Publication Date (Web): August 27, 2010 (Letter) DOI: 10.1021/ol101751d

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Stereodivergent Construction of Aminodiols with a CF3 Group

Abstract | Supporting Info

Ryusuke Obinata, Tomoko Kawasaki-Takasuka, and Takashi Yamazaki pp 4316–4319 Publication Date (Web): September 7, 2010 (Letter) DOI: 10.1021/ol101459a

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Palladium-Catalyzed Direct Arylation of Free NH2-Substituted Thiophene Derivatives

Abstract | Supporting Info

Fazia Derridj, Julien Roger, Safia Djebbar, and Henri Doucet pp 4320–4323 Publication Date (Web): September 1, 2010 (Letter) DOI: 10.1021/ol101758w

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Carbanionic Route to Electroactive Carbon-Centered Anion and Radical Oligomers

Abstract | Supporting Info

Eric L. Dane and Timothy M. Swager pp 4324–4327 Publication Date (Web): September 10, 2010 (Letter) DOI: 10.1021/ol1017728

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Synthesis of a Lactone Diastereomer of the Cembranolide Uprolide D

Abstract | Supporting Info

James A. Marshall, Céline A. Griot, Harry R. Chobanian, and William H. Myers pp 4328–4331 Publication Date (Web): August 26, 2010 (Letter) DOI: 10.1021/ol101776e

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Palladium-Catalyzed [4 + 2] Cycloaddition of o-(Silylmethyl)benzyl Esters with Ketones: An Equivalent to Oxo-Diels−Alder Reaction of o-Xylylenes Satoshi Ueno, Masakazu Ohtsubo, and Ryoichi Kuwano pp 4332–4334 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101792a

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Enantioselective 1,6-Conjugate Addition to Cyclic Dienones Catalyzed by the Cu−DiPPAM Complex Joanna Wencel-Delord, Alexandre Alexakis, Christophe Crévisy, and Marc Mauduit pp 4335–4337 Publication Date (Web): September 1, 2010 (Letter) DOI: 10.1021/ol1017382

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Facile Iterative Synthesis of Biphenyl Dendrons with a Functionalized Focus

Abstract | Supporting Info

Ellen J. Wren, Xin Wang, Anthony Farlow, Shih-Chun Lo, Paul L. Burn, and Paul Meredith pp 4338–4340 Publication Date (Web): September 8, 2010 (Letter) DOI: 10.1021/ol101717c

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Abstract | Supporting Info

O-Silylative Passerini Reaction: A New One-Pot Synthesis of -Siloxyamides Takahiro Soeta, Yuuki Kojima, Yutaka Ukaji, and Katsuhiko Inomata pp 4341–4343 Publication Date (Web): September 7, 2010 (Letter) DOI: 10.1021/ol101763w

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Enantioselective Synthesis of (Z)-1,2-anti-2,5-anti-Triol Monosilyl Ethers Using a CrossMetathesis Allylboration Sequence

Abstract | Supporting Info

SusAnn M. Winbush and William R. Roush pp 4344–4347 Publication Date (Web): August 31, 2010 (Letter) DOI: 10.1021/ol101789g

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Ni(0)-Catalyzed 1,4-Selective Diboration of Conjugated Dienes

Abstract | Supporting Info

Robert J. Ely and James P. Morken pp 4348–4351 Publication Date (Web): September 9, 2010 (Letter) DOI: 10.1021/ol101797f

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Organocatalytic Asymmetric Synthesis of Chiral Pyrrolizines by Cascade Conjugate Addition −Aldol Reactions Ju-Yeon Bae, Hyo-Jun Lee, Seok-Ho Youn, Su-Hyun Kwon, and Chang-Woo Cho pp 4352–4355 Publication Date (Web): August 26, 2010 (Letter) DOI: 10.1021/ol101811c

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Isolation of Putative Biosynthetic Intermediates of Prenylated Indole Alkaloids from a Thermophilic Fungus Talaromyces thermophilus

Abstract | Supporting Info

Yan-Sheng Chu, Xue-Mei Niu, Yan-Li Wang, Ji-Peng Guo, Wen-Zheng Pan, Xiao-Wei Huang, and Ke-Qin Zhang pp 4356–4359 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101817g

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DIBPillar[n]arenes (n = 5, 6): Syntheses, X-ray Crystal Structures, and Complexation with nOctyltriethyl Ammonium Hexafluorophosphate Chengyou Han, Fengying Ma, Zibin Zhang, Binyuan Xia, Yihua Yu, and Feihe Huang pp 4360–4363 Publication Date (Web): September 10, 2010 (Letter) DOI: 10.1021/ol1018344

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Synthesis of 1,4-Bis[2,2-bis(4-alkoxyphenyl)vinyl]benzenes and Side Chain Modulation of Their Solid-State Emission

Abstract | Supporting Info

Peng An, Zi-Fa Shi, Wei Dou, Xiao-Ping Cao, and Hao-Li Zhang pp 4364–4367 Publication Date (Web): September 7, 2010 (Letter) DOI: 10.1021/ol101847w

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Rapid Formation of Hindered Cores Using an Oxidative Prins Process

Abstract | Supporting Info

Jean-Christophe Andrez, Marc-André Giroux, Jessica Lucien, and Sylvain Canesi pp 4368–4371 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101851z

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Addition/Correction

3-Benzyl-3-azabicyclo[3.1.1]heptan-6-one: A Promising Building Block for Medicinal Chemistry

Abstract | Supporting Info

Aleksandr V. Denisenko, Andrey P. Mityuk, Oleksandr O. Grygorenko, Dmytro M. Volochnyuk, Oleg V. Shishkin, Andrey A. Tolmachev, and Pavel K. Mykhailiuk pp 4372–4375 Publication Date (Web): August 26, 2010 (Letter) DOI: 10.1021/ol101866x

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A New Strategy for the Synthesis of Poly-Substituted 3-H, 3-Fluoro, or 3-Trifluoromethyl Pyridines via the Tandem C−F Bond Cleavage Protocol

Abstract | Supporting Info

Zixian Chen, Jiangtao Zhu, Haibo Xie, Shan Li, Yongming Wu, and Yuefa Gong pp 4376–4379 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101859p

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Construction of Methylenecycloheptane Frameworks through 7-Exo-Dig Cyclization of Acetylenic Silyl Enol Ethers Catalyzed by Triethynylphosphine−Gold Complex

Abstract | Supporting Info

Hideto Ito, Hirohisa Ohmiya, and Masaya Sawamura pp 4380–4383 Publication Date (Web): September 7, 2010 (Letter) DOI: 10.1021/ol101860j

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Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Enantiomerically Enriched Potassium -Trifluoroboratoamides with Various Aryl- and Hetaryl Chlorides

Abstract | Supporting Info

Gary A. Molander, Inji Shin, and Ludivine Jean-Gérard pp 4384–4387 Publication Date (Web): September 10, 2010 (Letter) DOI: 10.1021/ol101865e

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Room Temperature Palladium-Catalyzed Cross Coupling of Aryltrimethylammonium Triflates with Aryl Grignard Reagents Jonathan T. Reeves, Daniel R. Fandrick, Zhulin Tan, Jinhua J. Song, Heewon Lee, Nathan K. Yee, and Chris H. Senanayake pp 4388–4391 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol1018739

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An Asymmetric Hydrogenation Route To (−)-Spongidepsin

Abstract | Supporting Info

Ye Zhu, Aurore Loudet, and Kevin Burgess pp 4392–4395 Publication Date (Web): September 7, 2010 (Letter) DOI: 10.1021/ol1018773

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Gold(I)-Catalyzed Cyclization of -Allenylhydrazones: An Efficient Synthesis of Multisubstituted N-Aminopyrroles

Abstract | Supporting Info

Erica Benedetti, Gilles Lemière, Laure-Lise Chapellet, Andrea Penoni, Giovanni Palmisano, Max Malacria, JeanPhilippe Goddard, and Louis Fensterbank pp 4396–4399 Publication Date (Web): September 8, 2010 (Letter) DOI: 10.1021/ol101889h

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Enantiopure 1,2-Bis(tert-butylmethylphosphino)benzene as a Highly Efficient Ligand in Rhodium-Catalyzed Asymmetric Hydrogenation

Abstract | Supporting Info

Ken Tamura, Masashi Sugiya, Kazuhiro Yoshida, Akira Yanagisawa, and Tsuneo Imamoto pp 4400–4403 Publication Date (Web): September 10, 2010 (Letter) DOI: 10.1021/ol101936w

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Scaparvin A, A Novel Caged cis-Clerodane with an Unprecedented C-6/C-11 Bond, and Related Diterpenoids from the Liverwort Scapania parva

Abstract | Supporting Info

Dong-Xiao Guo, Rong-Xiu Zhu, Xiao-Ning Wang, Li-Ning Wang, Shu-Qi Wang, Zhao-Min Lin, and Hong-Xiang Lou pp 4404–4407 Publication Date (Web): September 10, 2010 (Letter) DOI: 10.1021/ol1019458

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Copper-Catalyzed Nitrogen Loss of Sulfonylhydrazones: A Reductive Strategy for the Synthesis of Sulfones from Carbonyl Compounds

Abstract | Supporting Info

Xing-Wen Feng, Jian Wang, Ji Zhang, Jing Yang, Na Wang, and Xiao-Qi Yu pp 4408–4411 Publication Date (Web): September 2, 2010 (Letter) DOI: 10.1021/ol101955x

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Efficient Synthesis of a Small Molecule, Nonpeptide Inhibitor of LFA-1

Abstract | Supporting Info

Xiao-jun Wang, Yibo Xu, Li Zhang, Dhileepkumar Krishnamurthy, Thomas Wirth, Thomas Nicola, and Chris H. Senanayake pp 4412–4415 Publication Date (Web): September 10, 2010 (Letter) DOI: 10.1021/ol101960x

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Enantioselective Total Synthesis of Spirofungins A and B

Abstract | Supporting Info

Michael T. Crimmins and Elizabeth A. O’Bryan pp 4416–4419 Publication Date (Web): September 10, 2010 (Letter) DOI: 10.1021/ol101961c

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Efficient Synthetic Approach to Potent Antiproliferative Agent Hippuristanol via Hg(II)Catalyzed Spiroketalization

Abstract | Supporting Info

Kontham Ravindar, Maddi Sridhar Reddy, Lisa Lindqvist, Jerry Pelletier, and Pierre Deslongchamps pp 4420–4423 Publication Date (Web): September 9, 2010 (Letter) DOI: 10.1021/ol1019663

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Dinaphthoporphycenes

Abstract | Supporting Info

Vladimir Roznyatovskiy, Vincent Lynch, and Jonathan L. Sessler pp 4424–4427 Publication Date (Web): September 1, 2010 (Letter) DOI: 10.1021/ol101931y

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One-Pot Desulfurative−Fluorination−Bromination. Synthesis of 2,5-Dibromo-3-(1,1difluoroalkyl)thiophenes

Abstract | Supporting Info

Nashaat Turkman, Lingling An, and Martin Pomerantz pp 4428–4430 Publication Date (Web): August 30, 2010 (Letter) DOI: 10.1021/ol101907k

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Site-Selective Modification of Vitamin D Analogue (Deltanoid) through a Resin-Based Version of Organoselenium 2,3-Sigmatropic Rearrangement Wei-Ming Xu, Jun He, Min-Qiang Yu, and Guo-Xiang Shen pp 4431–4433 Publication Date (Web): September 9, 2010 (Letter) DOI: 10.1021/ol101879k

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