Total synthesis of plukenetione A

J Am Chem Soc. 2010 Oct 13;132(40):14212-5. doi: 10.1021/ja105784s.

Abstract

We describe an alkylative dearomatization/acid-mediated adamantane annulation sequence that allows facile access to type A polyprenylated acylphloroglucinol natural products including plukenetione A. Introduction of the 2-methyl-1-propenyl moiety was achieved via stereodivergent S(N)2 and S(N)1 cyclizations of allylic alcohol substrates.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkylation
  • Cyclization
  • Models, Molecular
  • Molecular Structure
  • Polycyclic Compounds / chemical synthesis*

Substances

  • Polycyclic Compounds
  • plukenetione A