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Journal article

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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APA Style

Robertson, J., North, C., & Sadig, J. (2011). Asymmetric synthesis of the C(6-18) bis(tetrahydropyran)spiroacetal fragment of the lituarines. TETRAHEDRON, 67(27-28), 5011–5023.

MLA Style

Robertson, J., et al. “Asymmetric Synthesis of the C(6-18) Bis(Tetrahydropyran)Spiroacetal Fragment of the Lituarines.” TETRAHEDRON, vol. 67, no. 27-28, 2011, pp. 5011–23.

Chicago Style

Robertson, J, C North, and J Sadig. 2011. “Asymmetric Synthesis of the C(6-18) Bis(Tetrahydropyran)Spiroacetal Fragment of the Lituarines.” TETRAHEDRON 67 (27-28): 5011–23.
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Publisher copy:: 10.1016/j.tet.2011.03.116

Authors

+ Robertson, J More by this author

Institution:

University of Oxford

Division:

MPLS

Department:

Chemistry

Sub department:

Organic Chemistry

Role:

Author

+ North, C More by this author

Role:

Author

+ Sadig, J More by this author

Role:

Author

Bibliographic Details

Journal:: TETRAHEDRON
Volume:: 67
Issue:: 27-28
Pages:: 5011-5023
Publication date:: 2011-07-08
DOI:: 10.1016/j.tet.2011.03.116
EISSN:: 1464-5416
ISSN:: 0040-4020

Item Description

Language:: English
Keywords:: Cyanohydrin

Oxy-Michael

Achmatowicz

Asymmetric

Diastereoselective
Pubs id:: pubs:167630
UUID:: uuid:61d37a5e-092a-43e1-bef0-ce9d6e365cd9
Local pid:: pubs:167630
Source identifiers:: 167630
Deposit date:: 2012-12-19

Terms of use

Copyright date:: 2011

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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