Synthesis and confirmation of the absolute stereochemistry of the (-)-aflastatin A C9-C27 degradation polyol.
[reaction: see text]. The C(8)-C(18) ethyl ketone and C(19)-C(28) aldehyde aflastatin A fragments were synthesized and coupled using a diastereoselective anti aldol reaction. This adduct was successfully converted into the C(9)-C(27) polyol degradation product of (-)-aflastatin A to confirm the relative and absolute stereochemistry of this region of the natural product.
Evans
David A
DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.edu
Trenkle
William C
WC
Zhang
Jing
J
Burch
Jason D
JD
D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D011108:Polymers; D011760:Pyrrolidinones; C105377:aflastatin A; C024617:polyol