Complex aldol reactions for the construction of dense polyol stereoarrays: synthesis of the C33-C36 region of aflastatin A.
[reaction: see text]. Facial selectivity in the addition of boron enolates of alpha-oxygenated ketones to anti-disposed alpha,beta-bisalkoxy aldehydes is controlled by the aldehyde vicinal diol protecting group. Protection of the diol as an acetonide results in the exclusive formation of the anti-syn-anti stereoarray found in the C(33)-C(36) region of aflastatin A.
Evans
David A
DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Glorius
Frank
F
Burch
Jason D
JD
D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D001896:Boron Compounds; D011760:Pyrrolidinones; C105377:aflastatin A