Total synthesis of (+)-quassin

J Org Chem. 2000 Oct 20;65(21):7059-69. doi: 10.1021/jo000877g.

Abstract

A total synthesis of (+)-quassin from naturally occurring (S)-(+)-carvone is described. The total number of steps was 28, and the overall yield was about 2.6%. The synthetic strategy for the construction of the tetracyclic carbon framework was based on a C-->ABC-->ABCD ring annulation sequence, involving an aldol reaction, an intramolecular Diels-Alder reaction, and an intramolecular acylation as the key steps. Subsequent functionalization of ring A and ring C then afforded the target (+)-quassin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Glaucarubin / analogs & derivatives*
  • Glaucarubin / chemical synthesis
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Quassins*
  • Stereoisomerism

Substances

  • Antineoplastic Agents, Phytogenic
  • Indicators and Reagents
  • Quassins
  • Glaucarubin
  • quassin