Stereoselective total synthesis of (±)-hyperforin via intramolecular cyclopropanation

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Total synthesis of (±)-hyperforin is described. This total synthesis features an approach via a bicyclo[ 3.3.1]nonane derivative prepared by a three-step sequence: intramolecular cyclopropanation, construction of the C8 all-carbon quaternary stereogenic center, and subsequent regioselective ring opening of cyclopropane. Further steps to obtain (±)-hyperforin include chemo- and stereoselective hydrogenation to generate the C7 stereogenic center, formation of the C9 isopropyl ketone using an organocerium reagent, and cross-metathesis at high temperatures to construct trisubstituted alkenes in side-chains.

Original languageEnglish
Pages (from-to)2022-2025
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number15
DOIs
Publication statusPublished - 2013 Apr 10

Fingerprint

Hydrogenation
Alkenes
Ketones
Carbon
Derivatives
Temperature
hyperforin
cyclopropane
bicyclo(3.3.1)nonane

Keywords

  • Cyclopropanation
  • Hyperforin
  • Natural product
  • Stereoselectivity
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective total synthesis of (±)-hyperforin via intramolecular cyclopropanation. / Uwamori, Masahiro; Nakada, Masahisa.

In: Tetrahedron Letters, Vol. 54, No. 15, 10.04.2013, p. 2022-2025.

Research output: Contribution to journalArticle

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