Journal article

Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement.

Abstract:: Starting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled Rh(II) -catalysed oxonium ylide formation-[2,3] sigmatropic rearrangement of an α-diazo-β-ketoester bearing allylic ether functionality. From the resulting furanone, an acid-catalysed lactonisation and dehydrogenation gives the natural product.

Publication status:: Published

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APA Style

Hodgson, D., & Man, S. (2011). Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement. Chemistry (Weinheim an Der Bergstrasse, Germany), 17(35), 9731–9737.

MLA Style

Hodgson, D., and S. Man. “Synthesis of the Anti-HIV Agent (-)-Hyperolactone C by Using Oxonium Ylide Formation-Rearrangement.” Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 17, no. 35, 2011, pp. 9731–37.

Chicago Style

Hodgson, D, and S Man. 2011. “Synthesis of the Anti-HIV Agent (-)-Hyperolactone C by Using Oxonium Ylide Formation-Rearrangement.” Chemistry (Weinheim an Der Bergstrasse, Germany) 17 (35): 9731–37.
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Publisher copy:: 10.1002/chem.201101082

Authors

+ Hodgson, D More by this author

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

+ Man, S More by this author

Role:: Author

Journal:: Chemistry (Weinheim an der Bergstrasse, Germany) More from this journal
Volume:: 17
Issue:: 35
Pages:: 9731-9737
Publication date:: 2011-08-01
DOI:: 10.1002/chem.201101082
EISSN:: 1521-3765
ISSN:: 0947-6539

Language:: English
Keywords:: Anti-HIV Agents

Catalysis

Epoxy Compounds

Stereoisomerism

Furans

Onium Compounds

Molecular Structure

Rhodium
Pubs id:: pubs:166433
UUID:: uuid:651e0cbb-2f02-4dce-8a70-c1c662723b9b
Local pid:: pubs:166433
Source identifiers:: 166433
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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