General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form

…, JS Carlson, CD Vanderwal

Index: Chung, Won-Jin; Carlson, Joseph S.; Vanderwal, Christopher D. Journal of Organic Chemistry, 2014 , vol. 79, # 5 p. 2226 - 2241

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Citation Number: 20

Abstract

A second-generation synthesis of three structurally related chlorosulfolipids has been developed. Key advances include highly stereocontrolled additions to α, β- dichloroaldehydes, kinetic resolutions of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metatheses of cis-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamensilipin A in nine, ...