jo5000829_si_001.pdf (3.03 MB)
General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form
journal contribution
posted on 2015-12-17, 00:55 authored by Won-jin Chung, Joseph S. Carlson, Christopher D. VanderwalA 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.