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Published on: August 12, 2019
Cafestol to Tricalysiolide B and Oxidized Analogues: Biosynthetic and Derivatization Studies Using Non-heme Iron
Marinus A Bigi1, Peng Liu, Lufeng Zou
1Roger 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.
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