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

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 <i>Z</i>-selective alkene cross metatheses of <i>cis</i>-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamen­silipin A in nine, eight, and 11 steps, respectively.