Journal article
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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Authors
Bibliographic Details
- Journal:
- TETRAHEDRON
- Volume:
- 59
- Issue:
- 49
- Pages:
- 9719-9728
- Publication date:
- 2003-12-01
- DOI:
- ISSN:
-
0040-4020
- Source identifiers:
-
38884
Item Description
- Language:
- English
- Keywords:
- Pubs id:
-
pubs:38884
- UUID:
-
uuid:36f926a5-45e9-42b8-99d1-c984df23c858
- Local pid:
- pubs:38884
- Deposit date:
- 2012-12-19
Terms of use
- Copyright date:
- 2003
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