A concise enantioselective synthesis of the chlorosulfolipid malhamensilipin A.
The first enantioselective synthesis of a member of the chlorosulfolipid family of natural products is reported. All of the polar substituents of malhamensilipin A are introduced with high stereoselectivity, and the unique (E)-chlorovinyl sulfate is created by a chemo-, regio-, and stereoselective E2 elimination of HCl in a reaction that likely has a counterpart in the biosynthesis of this fascinating natural product.
Bedke
D Karl
DK
Department of Chemistry, University of California, Irvine, California 92697, USA.
Shibuya
Grant M
GM
Pereira
Alban R
AR
Gerwick
William H
WH
Vanderwal
Christopher D
CD
D001688:Biological Products / Q000138:chemical synthesis*; D056890:Eukaryota / Q000737:chemistry; D008055:Lipids / Q000138:chemical synthesis*; D015394:Molecular Structure; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
D001688:Biological Products; D008055:Lipids; C088109:malhamensilipin A; D011505:Protein-Tyrosine Kinases