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

Overview

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 1, 2003

Research

keywords

  • Sesquiterpenes

Identity

Scopus Document Identifier

  • 0038336109

Digital Object Identifier (DOI)

  • 10.1021/np0205607

PubMed ID

  • 12713405

Additional Document Info

volume

  • 66

issue

  • 4