RESUMO

A concise nonaldol approach for the stereoselective construction of all-anti polypropionate fragments was developed. The iterative epoxide-based methodology consists of the syn-selective epoxidation of cis homoallylic alcohols with use of the VO(acac)(2)-catalyzed conditions followed by epoxide cleavage with a propynyl aluminum reagent as key steps. The methodology was applied to the synthesis of the all-anti C6-C10 fragment of streptovaricin U.

Assuntos

Macrolídeos/síntese química , Propionatos/química , Propionatos/síntese química , Catálise , Compostos de Epóxi/química , Estereoisomerismo