Conversion of optically active hydrindanone to (+)-bakkenolide-A

Chem Pharm Bull (Tokyo). 2008 Oct;56(10):1436-7. doi: 10.1248/cpb.56.1436.

Abstract

A total synthesis of (+)-bakkenolide-A was carried out via the key intermediate 4, which was prepared based on an asymmetric cyclization-carbonylation reaction established in our laboratory. Diastereoselective construction of the spirolactone moiety was achieved using Mitsuhashi's protocol as a key step.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Cyclization
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Sesquiterpenes
  • Spironolactone / chemical synthesis
  • Spironolactone / chemistry
  • Stereoisomerism

Substances

  • Antineoplastic Agents, Phytogenic
  • Indicators and Reagents
  • Sesquiterpenes
  • Spironolactone
  • 4-Butyrolactone
  • bakkenolide A