Total synthesis of the purported structure of sclerophytin F

Clark, J. S. , Delion, L. and Farrugia, L. J. (2014) Total synthesis of the purported structure of sclerophytin F. Organic Letters, 16(16), pp. 4300-4303. (doi: 10.1021/ol5020152)

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 natu-ral 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 3S configuration (*) proposed previously.

• Item Type: Articles (Letter)
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Clark, Professor Stephen and Farrugia, Dr Louis and Delion, Miss Laetitia
• Authors: Clark, J. S., Delion, L., and Farrugia, L. J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• Journal Abbr.: Org. Lett.
• Publisher: American Chemical Society
• ISSN: 1523-7060
• ISSN (Online): 1523-7052
• Copyright Holders: Copyright © 2014 American Chemical Society
• First Published: First published in Organic Letters 16(16):4300-4303
• Publisher Policy: Reproduced in accordance with the copyright policy of the publisher.