Controlling the Facial Selectivity of Asymmetric [4+2] Cyclo-additions: A Concise Synthesis of the cis-Decalin Core Structure of Superstolides A and B

Lei Chen; Zhengmao Hua; Gangqin Li; Zhendong Jin

doi:10.1021/ol201095b

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Controlling the Facial Selectivity of Asymmetric [4+2] Cyclo-additions: A Concise Synthesis of the cis-Decalin Core Structure of Superstolides A and B

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Controlling the Facial Selectivity of Asymmetric [4+2] Cyclo-additions: A Concise Synthesis of the cis-Decalin Core Structure of Superstolides A and B

Lei Chen, Zhengmao Hua, Gangqin Li and Zhendong Jin

Organic letters, Vol.13(14), pp.3580-3583

07/15/2011

DOI: 10.1021/ol201095b

PMCID: PMC3132299

PMID: 21671636

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Abstract

Reglo-, stereo-, and facial selective [4 + 2] cycloadditions between highly activated vinyl sulfones and 1,3-dienes derived from (R)-4-tert-wbutyldimethylsilyloxy-2-cyclohexen-1-one provide a powerful approach for the asymmetric synthesis of compounds containing the bicyclo[2.2.2]octanone carbon skeleton. This new methodology has been successfully applied to the asymmetric synthesis of the cis-decalin core structure of the potent anticancer marine natural products superstolides A and B.

Chemistry

Chemistry, Organic

Physical Sciences

Science & Technology

Details

Title: Subtitle: Controlling the Facial Selectivity of Asymmetric [4+2] Cyclo-additions: A Concise Synthesis of the cis-Decalin Core Structure of Superstolides A and B
Creators: Lei Chen - Univ Iowa, Coll Pharm, Div Med & Nat Prod Chem, Dept Pharmaceut Sci & Expt Therapeut, Iowa City, IA 52242 USA
Zhengmao Hua - University of Iowa
Gangqin Li - Univ Iowa, Coll Pharm, Div Med & Nat Prod Chem, Dept Pharmaceut Sci & Expt Therapeut, Iowa City, IA 52242 USA
Zhendong Jin - University of Iowa
Resource Type: Journal article
Publication Details: Organic letters, Vol.13(14), pp.3580-3583
Publisher: Amer Chemical Soc
DOI: 10.1021/ol201095b
PMID: 21671636
PMCID: PMC3132299
ISSN: 1523-7060
eISSN: 1523-7052
Number of pages: 4
Grant note: R01CA109208 / NATIONAL CANCER INSTITUTE; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Cancer Institute (NCI) R01 CA109208 / NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA
Language: English
Date published: 07/15/2011
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
Record Identifier: 9984365905002771

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