Tandem oxidative dearomatization/intramolecular Diels-Alder reaction for construction of the tricyclic core of palhinine A

Org Lett. 2012 May 4;14(9):2293-5. doi: 10.1021/ol3007138. Epub 2012 Apr 12.

Abstract

A concise construction of the 6/6/5 tricyclic core of Lycopodium alkaloid palhinine A (1) has been accomplished. The developed synthetic strategy featured a tandem oxidative dearomatization/intramolecular Diels-Alder reaction to construct C/D rings and an intramolecular 5-exo-trig radical cyclization to install the B ring of palhinine A (1). The developed approach paves the way for the total synthesis of palhinine A (1).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Cyclization
  • Lycopodium / chemistry
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Alkaloids
  • palhinine A