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

doi:10.1055/s-0032-1317708

Cafestol to Tricalysiolide B and Oxidized Analogues: Biosynthetic and Derivatization Studies Using Non-heme Iron Catalyst Fe(PDP)

Synlett. 2012 Dec 1;23(19):2768-2772. doi: 10.1055/s-0032-1317708.

Authors

Marinus A Bigi¹, Peng Liu, Lufeng Zou, K N Houk, M Christina White

Affiliation

¹ Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA, Fax +1(217)2445943.

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.

Keywords: C–H oxidation; aliphatic; biosynthesis; cafestol; functionalization; natural product diversification; non-heme iron.

Abstract

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