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 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.
Department of Chemistry, 1102 Natural Sciences II, University of California , Irvine, California 92697-2025, United States.
Won-jin
WJ
Chung
Joseph S
JS
Carlson
Christopher D
CD
Vanderwal
D007700:Kinetics; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D008055:Lipids; D014753:Vinyl Compounds; C557671:danicalipin A; C088109:malhamensilipin A