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

  • Author(s): Chung, Won-jin
  • Carlson, Joseph S
  • Vanderwal, Christopher D
  • et al.

Published Web Location

https://doi.org/10.1021/jo5000829Creative Commons 'BY' version 4.0 license
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, eight, and 11 steps, respectively.

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