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Updated: Aug 5, 2026

Isolation and Compositional Analysis of Plant Cuticle Lipid Polyester Monomers
Published on: November 22, 2015
Total synthesis of the purported structure of sclerophytin F
J Stephen Clark1, Laetitia Delion, Louis J Farrugia
1WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow , University Avenue, Glasgow, G12 8QQ, United Kingdom.
Abstract:
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.
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