Journal article

Progress in the synthesis of the lituarines: stereocontrol in sequential C-C bond formation on a spirobutenolide template.

Abstract:: [structure: see text] We describe elaboration of a tricyclic spirobutenolide corresponding to the C(7-18) tricyclic substructure common to lituarines A-C. Conjugate addition, to install the C(16) methyl, is followed by construction of the crucial C(18-19) bond by silyl enol ether addition to the derived spiroacetal C(18)-O oxonium ion. Esterification with a C(1-6) acid, and selective ozonolysis to release the C(23) carbonyl, complete the assembly of all the carbons present in the lituarine macrocyclic core.

Publication status:: Published

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APA Style

Robertson, J., & Dallimore, J. (2005). Progress in the synthesis of the lituarines: stereocontrol in sequential C-C bond formation on a spirobutenolide template. Organic Letters, 7(22), 5007–5010.

MLA Style

Robertson, J, and J Dallimore. “Progress in the Synthesis of the Lituarines: Stereocontrol in Sequential C-C Bond Formation on a Spirobutenolide Template.” Organic Letters, vol. 7, no. 22, 2005, pp. 5007–10.

Chicago Style

Robertson, J, and J Dallimore. 2005. “Progress in the Synthesis of the Lituarines: Stereocontrol in Sequential C-C Bond Formation on a Spirobutenolide Template.” Organic Letters 7 (22): 5007–10.
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Publisher copy:: 10.1021/ol0520018

Authors

+ Robertson, J More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Dallimore, J More by this author

Role:: Author

Journal:: Organic letters More from this journal
Volume:: 7
Issue:: 22
Pages:: 5007-5010
Publication date:: 2005-10-01
DOI:: 10.1021/ol0520018
EISSN:: 1523-7052
ISSN:: 1523-7060

Language:: English
Keywords:: Epoxy Compounds

Carbon

Macrocyclic Compounds

Spiro Compounds

Molecular Structure

4-Butyrolactone

Stereoisomerism
Pubs id:: pubs:55226
UUID:: uuid:85234bc7-e11a-4e92-967e-7287cf75ee58
Local pid:: pubs:55226
Source identifiers:: 55226
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_85234bc7e11a4e92967e7287cf75ee58

Terms of use

Copyright date:: 2005

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

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