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

52 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

Access to Document

10.1073/pnas.0402563101

Cite this

@article{308fc9b51e4d47c3b1d7d598ff222c8b,

title = "A nucleophile-catalyzed cycloisomerization permits a concise synthesis of (+)-harziphilone",

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.",

keywords = "Baylis-Hillman reaction, Conjugate additions, Domino reactions, Electrocyclizations, Nucleophilic catalysis",

author = "Stark, {Lucy M.} and Klaus Pekari and Sorensen, {Erik J.}",

year = "2004",

month = aug,

day = "17",

doi = "10.1073/pnas.0402563101",

language = "English (US)",

volume = "101",

pages = "12064--12066",

journal = "Proceedings of the National Academy of Sciences of the United States of America",

issn = "0027-8424",

publisher = "National Academy of Sciences",

number = "33",

}

TY - JOUR

T1 - A nucleophile-catalyzed cycloisomerization permits a concise synthesis of (+)-harziphilone

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

UR - http://www.scopus.com/inward/record.url?scp=4344625385&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=4344625385&partnerID=8YFLogxK

U2 - 10.1073/pnas.0402563101

DO - 10.1073/pnas.0402563101

M3 - Article

C2 - 15232001

AN - SCOPUS:4344625385

SN - 0027-8424

VL - 101

SP - 12064

EP - 12066

JO - Proceedings of the National Academy of Sciences of the United States of America

JF - Proceedings of the National Academy of Sciences of the United States of America

IS - 33

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Access to Document

Other files and links

Fingerprint

Cite this