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Synlett 2012; 23(19): 2768-2772
DOI: 10.1055/s-0032-1317708
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© Georg Thieme Verlag Stuttgart · New York

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

Marinus A. Bigi
a   Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA   Fax: +1(217)2445943   Email: white@scs.uiuc.edu
,
Peng Liu
b   Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA   Fax: +(310)2061843   Email: houk@chem.ucla.edu
,
Lufeng Zou
b   Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA   Fax: +(310)2061843   Email: houk@chem.ucla.edu
,
K. N. Houk*
b   Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA   Fax: +(310)2061843   Email: houk@chem.ucla.edu
,
M. Christina White*
a   Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA   Fax: +1(217)2445943   Email: white@scs.uiuc.edu
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Publication History

Received: 19 October 2012

Accepted after revision: 09 November 2012

Publication Date:
14 November 2012 (online)

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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.

Key words

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

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