American Chemical Society
Browse
ol5020152_si_003.cif (154.3 kB)

Total Synthesis of the Purported Structure of Sclerophytin F

Download (154.3 kB)
dataset
posted on 2014-08-15, 00:00 authored by J. Stephen Clark, Laetitia Delion, Louis J. Farrugia
The synthesis of the compound that has been proposed to be the natural product sclerophytin F has been completed from a known vinylogous carbonate. The synthetic strategy relied upon rearrangement of a catalytically generated ylide-like intermediate to produce an oxa­bicyclo­[6.2.1]-5-undecen-9-one and an intermolecular Diels–Alder reaction to construct the complete tricyclic core found in the natural product. Comparison of the spectroscopic data for synthetic material to that reported for sclerophytin F shows that the natural product does not have the revised structure possessing the 3S configuration (*) proposed previously.

History