A nucleophile-catalyzed cycloisomerization permits a concise synthesis of (+)-harziphilone

Lucy M. Stark; Klaus Pekari; Erik J. Sorensen

doi:10.1073/pnas.0402563101

A nucleophile-catalyzed cycloisomerization permits a concise synthesis of (+)-harziphilone

Lucy M. Stark, Klaus Pekari, Erik J. Sorensen

Chemistry

Research output: Contribution to journal › Article › peer-review

54 Scopus citations

Abstract

Substantial structural transformations of much use in complex chemical synthesis can be achieved by channeling the reactivity of highly unsaturated molecules. This report describes the direct conversion of an acyclic polyunsaturated diketone to the HIV-1 Rev/Rev-responsive element inhibitor harziphilone under mild reaction conditions.

Original language	English (US)
Pages (from-to)	12064-12066
Number of pages	3
Journal	Proceedings of the National Academy of Sciences of the United States of America
Volume	101
Issue number	33
DOIs	https://doi.org/10.1073/pnas.0402563101
State	Published - Aug 17 2004

All Science Journal Classification (ASJC) codes

General

Keywords

Baylis-Hillman reaction
Conjugate additions
Domino reactions
Electrocyclizations
Nucleophilic catalysis

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10.1073/pnas.0402563101

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abstract = "Substantial structural transformations of much use in complex chemical synthesis can be achieved by channeling the reactivity of highly unsaturated molecules. This report describes the direct conversion of an acyclic polyunsaturated diketone to the HIV-1 Rev/Rev-responsive element inhibitor harziphilone under mild reaction conditions.",

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AU - Stark, Lucy M.

AU - Pekari, Klaus

AU - Sorensen, Erik J.

PY - 2004/8/17

Y1 - 2004/8/17

N2 - Substantial structural transformations of much use in complex chemical synthesis can be achieved by channeling the reactivity of highly unsaturated molecules. This report describes the direct conversion of an acyclic polyunsaturated diketone to the HIV-1 Rev/Rev-responsive element inhibitor harziphilone under mild reaction conditions.

AB - Substantial structural transformations of much use in complex chemical synthesis can be achieved by channeling the reactivity of highly unsaturated molecules. This report describes the direct conversion of an acyclic polyunsaturated diketone to the HIV-1 Rev/Rev-responsive element inhibitor harziphilone under mild reaction conditions.

KW - Baylis-Hillman reaction

KW - Conjugate additions

KW - Domino reactions

KW - Electrocyclizations

KW - Nucleophilic catalysis

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ER -

A nucleophile-catalyzed cycloisomerization permits a concise synthesis of (+)-harziphilone

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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