Total synthesis of (-)-saliniketals A and B

Org Lett. 2008 Aug 7;10(15):3295-8. doi: 10.1021/ol801148d. Epub 2008 Jun 26.

Abstract

A stereocontrolled total synthesis of the orthinine decarboxylase inhibitors saliniketals A and B is described. Key features of the 17-step route include the use of two boron aldol/reduction sequences to control six of the nine stereocenters, an intramolecular Wacker-type cyclization to install the bicyclic acetal core, and a late-stage Stille coupling to append the requisite (2 Z,4 E)-dienamide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Micromonosporaceae / chemistry
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • saliniketal A
  • saliniketal B