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Asymmetric synthesis of the C(6-18) bis(tetrahydropyran)spiroacetal fragment of the lituarines

Abstract:

We describe efforts to achieve a multigram synthesis of the tricyclic spiroacetal core of the lituarines based on the addition of acyl anion equivalent to 4-(2-furyl)butan-2-one (18). We report the first cases of chemoselective Achmatowicz reaction in the presence of a second furan ring that lacks an α-hydroxyl group. The use of lithiated methoxyallene provides an efficient one-step conversion of ketone 18 into a tricyclic Diels-Alder adduct (27). In the final route, asymmetric cyanosilylatio...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2011.03.116

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON More from this journal
Volume:
67
Issue:
27-28
Pages:
5011-5023
Publication date:
2011-07-08
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Language:
English
Keywords:
Pubs id:
pubs:167630
UUID:
uuid:61d37a5e-092a-43e1-bef0-ce9d6e365cd9
Local pid:
pubs:167630
Source identifiers:
167630
Deposit date:
2012-12-19

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