A ring-closing metathesis approach toward formal total synthesis of (+)-diplodialide A

J Org Chem. 2003 Apr 18;68(8):3356-9. doi: 10.1021/jo034049+.

Abstract

An asymmetric formal total synthesis of diplodialide A 1a has been achieved starting from methyl acetoacetate 6 and (R)-3-buten-2-ol 7. The macrocyclic ring core of (+)-diplodialide A 1a was constructed, in an excellent yield, by using a ring-closing metathesis strategy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry, Organic / methods*
  • Cyclization
  • Fungi / chemistry
  • Indicators and Reagents
  • Lactones / analysis
  • Lactones / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Lactones
  • diplodialide A