Collective total synthesis of PPAPs: Total synthesis of clusianone via intramolecular cyclopropanation

Masahiro Uwamori, Masahisa Nakada

Research output: Contribution to journalReview article

8 Citations (Scopus)

Abstract

The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- And stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the total synthesis of clusianone.

Original languageEnglish
Pages (from-to)955-959
Number of pages5
JournalNatural Product Communications
Volume8
Issue number7
Publication statusPublished - 2013 Aug 2

    Fingerprint

Keywords

  • Clusianone
  • Cyclopropanation
  • Natural product
  • Stereoselectivity
  • Total synthesis

ASJC Scopus subject areas

  • Pharmacology
  • Plant Science
  • Drug Discovery
  • Complementary and alternative medicine

Cite this