Anti aldol selectivity in a synthetic approach to the C1-C12 fragment of the tedanolides.
In a synthetic approach to the completely protected C1-C12 fragment of the macrocyclic cytotoxic agent tedanolide 1, we carried out the tin-catalyzed Mukaiyama aldol reaction between the 2,3-dialkoxypropanal 5 and the silyl enol ether 6 derived from the ketone 7, which gave, unexpectedly, the anti aldol isomer, rather than the expected syn isomer 4, as the major diastereomer formed.
Jung
Michael E
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu
Zhang
Ting-hu
TH
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D007659:Ketones; D007783:Lactones; D018942:Macrolides; C119775:tedanolide