Synthesis of four diastereomers of sclerophytin f and structural reassignment of several sclerophytin natural products

Clark, J. S. , Delion, L. and Farrugia, L. J. (2015) Synthesis of four diastereomers of sclerophytin f and structural reassignment of several sclerophytin natural products. Chemistry: A European Journal, 21(12), pp. 4772-4780. (doi:10.1002/chem.201406051) (PMID:25663662)

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Abstract

Synthesis of the triol that has been proposed to be the marine natural product sclerophytin F has been completed along with the syntheses of three diastereomers. Comparison of the NMR spectroscopic data for all four compounds to the data reported for the natural product reveals that sclerophytin F is not the 3S diastereomer of sclerophytin A as proposed by Friedrich and Paquette. Re-analysis of the NMR spectroscopic data for known sclerophytin natural products and synthetic analogues leads to the conclusion that sclerophytins E and F are the same compound. This finding has allowed structural reassignment of several other cladiellin natural products.

Item Type:Articles
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:Chemistry: A European Journal
Journal Abbr.:Chem. Eur J.
Publisher:Wiley-VCH Verlag
ISSN:0947-6539
ISSN (Online):1521-3765
Copyright Holders:Copyright © 2015 Wiley-VCH Verlag
First Published:First published in Chemistry: A European Journal 21(12):4772-4780
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher.

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