Cafestol to tricalysiolide B and oxidized analogues: Biosynthetic and derivatization studies using non-heme iron catalyst Fe(PDP)

Marinus A. Bigi, Peng Liu, Lufeng Zou, K. N. Houk, M. Christina White

Research output: Contribution to journalArticlepeer-review

Abstract

The tricalysiolides are a recently isolated class of diterpene natural products featuring the carbon backbone of the well-known coffee extract, cafestol. Herein we validate the use of our non-heme iron complex, Fe(PDP), as an oxidative tailoring enzyme mimic to test the proposal that this class of natural products derives from cafestol via cytochrome P-450-mediated furan oxidation. Thereafter, as predicted by computational analysis, C-H oxidation derivatization studies provided a novel 2° alcohol product as a single diastereomer.

Original languageEnglish (US)
Pages (from-to)2768-2772
Number of pages5
JournalSynlett
Volume23
Issue number19
DOIs
StatePublished - 2012

Keywords

  • C-H oxidation
  • aliphatic
  • biosynthesis
  • cafestol
  • functionalization
  • natural product diversification
  • non-heme iron

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Cafestol to tricalysiolide B and oxidized analogues: Biosynthetic and derivatization studies using non-heme iron catalyst Fe(PDP)'. Together they form a unique fingerprint.

Cite this