First total synthesis of the marine natural products clavulolactones II and III

Org Biomol Chem. 2015 Apr 7;13(13):4051-8. doi: 10.1039/c5ob00074b.

Abstract

The first total synthesis of the marine prostanoids clavulolactones II and III is presented from an easily accessible chiral, non-racemic cyclopentenone intermediate. Key steps involve selective TBDMS deprotection, selective reduction of the β-side chain and aldol condensation. Clavulolactones II and III were successfully prepared from (S)-4-((tert-butyldimethylsilyl)oxy) cyclopent-2-en-1-one over nine steps, in overall yields of 21 and 7% respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Chemistry Techniques, Synthetic
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry
  • Oceans and Seas*
  • Prostaglandins / chemical synthesis*
  • Prostaglandins / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Cyclopentanes
  • Prostaglandins
  • 4-Butyrolactone
  • cyclopentenone