Issue 4, 2009
From the journal:

Organic & Biomolecular Chemistry

Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis†

Amanda C. Evans,a   Deborah A. Longbottom,a   Masato Matsuoka,b   John E. Davies,a   Richard Turner,a   Vilius Franckevičiusa  and  Steven V. Ley*a  

* Corresponding authors

a University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, UK
E-mail: svl1000@cam.ac.uk
Fax: +44 (0)1223 336442

b Nippon Shinyaku Co., Ltd., 3-14-1 Sakura, Tsukuba, Japan

Abstract

A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.

Graphical abstract: Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

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Article information

DOI
https://doi.org/10.1039/B813494D
Article type
Paper
Submitted
04 Aug 2008
Accepted
10 Nov 2008
First published
06 Jan 2009

Org. Biomol. Chem., 2009,7, 747-760

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Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

A. C. Evans, D. A. Longbottom, M. Matsuoka, J. E. Davies, R. Turner, V. Franckevičius and S. V. Ley, Org. Biomol. Chem., 2009, 7, 747 DOI: 10.1039/B813494D

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