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Stereocontrolled syntheses of (-)-cubebol and (-)-10-epicubebol involving intramolecular cyclopropanation of alpha-lithiated epoxides.

Abstract:

Formylation of (-)-menthone (11) with LDA and HCO(2)CH(2)CF(3) avoids loss of configurational integrity at the isopropyl group, giving hydroxymethylenementhone 12. Lithium 2,2,6,6-tetramethylpiperidide-induced intramolecular cyclopropanation of derived unsaturated terminal epoxide 17 (and chlorohydrin 16), efficiently generates a substituted tricyclo[4.4.0.0(1,5)]decan-4-ol 18, which is used in a concise synthesis of (-)-cubebol (1). In contrast, isopropyl group inversion during formylation o...

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Publication status:
Published

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Publisher copy:
10.1021/jo9022974

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Journal of organic chemistry More from this journal
Volume:
75
Issue:
7
Pages:
2157-2168
Publication date:
2010-04-01
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Language:
English
Pubs id:
pubs:45926
UUID:
uuid:cd818399-416c-46eb-b9ca-b0f172e2e097
Local pid:
pubs:45926
Source identifiers:
45926
Deposit date:
2012-12-19

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