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