An efficient formal synthesis of the sesquiterpenoid longifolene Academic Article uri icon

Overview

MeSH Major

  • Sesquiterpenes

abstract

  • Through a convenient ring expansion reaction of key intermediate 1, enone 5, containing the longifolene skeleton, was produced. Elaboration of 5 via hydrogenation, Wittig reaction, Simmons-Smith reaction, and subsequent hydrogenolysis led to ketone 9. Reductive debromination of 9 afforded 10, the penultimate precursor to longifolene. This formal total synthesis was accomplished in 13 steps using commercially available Wieland-Miescher ketone as the starting material.

publication date

  • April 2003

Research

keywords

  • Academic Article

Identity

Language

  • eng

Digital Object Identifier (DOI)

  • 10.1021/np0205607

PubMed ID

  • 12713405

Additional Document Info

start page

  • 520

end page

  • 3

volume

  • 66

number

  • 4