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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.

Controlling the facial selectivity of asymmetric [4+2] cyclo-additions: a concise synthesis of the cis-decalin core structure of superstolides A and B.

Organic letters (2011-06-16)
Lei Chen, Zhengmao Hua, Gangqin Li, Zhendong Jin
ABSTRACT

Regio-, stereo-, and facial selective [4 + 2] cycloadditions between highly activated vinyl sulfones and 1,3-dienes derived from (R)-4-tert-butyldimethylsilyloxy-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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, reagent grade, 98%
Sigma-Aldrich
cis-Decahydronaphthalene, 99%
Sigma-Aldrich
trans-Decahydronaphthalene, 99%
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, anhydrous, ≥99%
Sigma-Aldrich
Divinyl sulfone, contains hydroquinone as inhibitor, ≥96%