Total synthesis of 20-norsalvinorin A. 1. Preparation of a key intermediate

J Org Chem. 2009 Mar 20;74(6):2589-91. doi: 10.1021/jo802623n.

Abstract

The key tricyclic intermediate 3a, for the total synthesis of the C(20)-nor analogue of salvinorin A, was prepared in seven steps from 3-furaldehyde. Key steps involved a highly regio- and diastereoselective Lewis acid assisted Diels-Alder reaction followed by base-promoted epimerization and a completely stereoselective conjugate reduction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diterpenes, Clerodane / chemical synthesis*
  • Furaldehyde / chemistry
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Stereoisomerism

Substances

  • Diterpenes, Clerodane
  • Heterocyclic Compounds, 3-Ring
  • Furaldehyde
  • salvinorin A