A Synthetic Approach to Several C7-Carbasugars via a Key Intramolecular Morita-Baylis-Hillman Reaction

J Org Chem. 2022 Nov 4;87(21):14636-14645. doi: 10.1021/acs.joc.2c01992. Epub 2022 Oct 12.

Abstract

A new synthetic strategy for C7-carbasugars is developed via an intramolecular Morita-Baylis-Hillman reaction, in which a substituted dial precursor prepared from d-mannose cyclizes smoothly in the presence of DMAP to afford polyhydroxylated cyclohex-1-enecarbaldehyde with good yield. By employment of the cyclization products as key intermediates, the first syntheses of carbasugar ester 1 and epicorepoxydon A, as well as practical syntheses of epoxydines B and C, (-)-MK7607, (-)-streptol, and (-)-gabosine E are achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbasugars*
  • Cyclization
  • Esters

Substances

  • Carbasugars
  • Esters