Stereoselective synthesis of a family of alternating polyols from six-carbon epoxyalkynol modules.
Our new synthetic strategy for assembling polyacetate structures features efficient cross-couplings of six-carbon modules derived from any stereoisomer of the epoxyalkynol derivative (1). Hydration of the internal alkyne in the coupled products and stereoselective reduction of the resulting ketone intermediate provides a general approach to a library of stereoisomeric 1, 3, 5, ... alternating polyols (2). The strategy is demonstrated in a stereoselective synthesis of the C11-C28 polyol substructure of the natural product RK-397.
Burova
Svetlana A
SA
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
McDonald
Frank E
FE
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000480:Alkynes; D004852:Epoxy Compounds; D011108:Polymers; C024617:polyol