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Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide

Abstract:
The first total synthesis of (-)-xialenon A was achieved via enantioselective transannular desymmetrisation of a substituted cycloctene oxide using an organolithium/(-)-α-isosparteine combination. Oxidation of the resulting bicyclo[3.3.0]octanol gave an enone which underwent stereoselective conjugate allylation; subsequent α′-hydroxylation on the more hindered face of a derived enone using hypervalent iodine chemistry led to the natural product. © 2003 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Publisher copy:
10.1016/j.tet.2003.09.023

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON
Volume:
59
Issue:
49
Pages:
9719-9728
Publication date:
2003-12-01
DOI:
ISSN:
0040-4020
Source identifiers:
38884
Language:
English
Keywords:
Pubs id:
pubs:38884
UUID:
uuid:36f926a5-45e9-42b8-99d1-c984df23c858
Local pid:
pubs:38884
Deposit date:
2012-12-19

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