title: Cafestol to Tricalysiolide B and Oxidized Analogues: Biosynthetic and Derivatization Studies Using Non-heme Iron Catalyst Fe(PDP).
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.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA, Fax +1(217)2445943.
authors.forename: Marinus A
authors.initials: MA
authors.lastname: Bigi
authors.forename: Peng
authors.initials: P
authors.lastname: Liu
authors.forename: Lufeng
authors.initials: L
authors.lastname: Zou
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
authors.forename: M Christina
authors.initials: MC
authors.lastname: White
keywords: C–H oxidation; aliphatic; biosynthesis; cafestol; functionalization; natural product diversification; non-heme iron