A novel, versatile D-->BCD steroid construction strategy, illustrated by the enantioselective total synthesis of estrone

Org Lett. 2010 Feb 19;12(4):680-3. doi: 10.1021/ol902638w.

Abstract

A general steroid synthesis is presented that relies on prior formation of three stereogenic centers (C8, C13, and C14) on a D ring template, followed by C- and B-ring cyclizations. The assembly of the key D ring template, achieved by a 3-component conjugate addition/alkylation process, allows introduction of structural variety as required. The method is illustrated by the total synthesis of estrone via a C-ring closing metathesis and a B-ring Heck cyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Catalysis
  • Cyclization
  • Estrone / chemical synthesis*
  • Estrone / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Estrone