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General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form

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journal contribution
posted on 17.12.2015, 00:55 authored by Won-jin Chung, Joseph S. Carlson, Christopher D. Vanderwal
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, eight, and 11 steps, respectively.