A Paterno-Büchi approach to the synthesis of merrilactone A

Org Lett. 2005 Sep 1;7(18):3969-71. doi: 10.1021/ol0514496.

Abstract

A six-step approach to the tetracyclic core of merrilactone A is described that uses an intramolecular Paterno-Büchi photoaddition to install the key oxetane ring. Irradiation of bicyclic enone 16, constructed through cyclopentenone alkylation followed by a domino oxy-/carbopalladation reaction, produces the tetracyclic oxetane 17 in excellent yield, having the core carbon skeleton of the target compound merrilactone A. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Catalysis
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Palladium / chemistry*
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry

Substances

  • Lactones
  • Sesquiterpenes
  • merrilactone A
  • Palladium