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)

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Publisher's URL: http://dx.doi.org/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.

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