Oxa-enediynes: Probing the electronic and stereoelectronic contributions to the bergman cycloaromatization

Graham B. Jones; Justin M. Wright; George Hynd; Justin K. Wyatt; Philip M. Warner; Robert S. Huber; Aiwen Li; Michael W. Kilgore; Robert P. Sticca; Richard S. Pollenz

doi:10.1021/jo0256888

Oxa-enediynes: Probing the electronic and stereoelectronic contributions to the bergman cycloaromatization

Graham B. Jones, Justin M. Wright, George Hynd, Justin K. Wyatt, Philip M. Warner, Robert S. Huber, Aiwen Li, Michael W. Kilgore, Robert P. Sticca, Richard S. Pollenz

Pharmacology and Nutritional Sciences

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

36 Scopus citations

Abstract

Efficient routes to three classes of 10-membered oxa-enediynes are presented. The electronic and stereoelectronic contributions to half-lives are supported by density functional theory calculations. One member of this class cyclizes to give an isochroman which binds to and degrades the aryl hydrocarbon receptor (AhR).

Original language	English
Pages (from-to)	5727-5732
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	67
Issue number	16
DOIs	https://doi.org/10.1021/jo0256888
State	Published - Aug 9 2002

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo0256888

Cite this

@article{f8cb6fb87c794cf685b85dcc6e7fe00d,

title = "Oxa-enediynes: Probing the electronic and stereoelectronic contributions to the bergman cycloaromatization",

abstract = "Efficient routes to three classes of 10-membered oxa-enediynes are presented. The electronic and stereoelectronic contributions to half-lives are supported by density functional theory calculations. One member of this class cyclizes to give an isochroman which binds to and degrades the aryl hydrocarbon receptor (AhR).",

author = "Jones, {Graham B.} and Wright, {Justin M.} and George Hynd and Wyatt, {Justin K.} and Warner, {Philip M.} and Huber, {Robert S.} and Aiwen Li and Kilgore, {Michael W.} and Sticca, {Robert P.} and Pollenz, {Richard S.}",

year = "2002",

month = aug,

day = "9",

doi = "10.1021/jo0256888",

language = "English",

volume = "67",

pages = "5727--5732",

number = "16",

}

TY - JOUR

T1 - Oxa-enediynes

T2 - Probing the electronic and stereoelectronic contributions to the bergman cycloaromatization

AU - Jones, Graham B.

AU - Wright, Justin M.

AU - Hynd, George

AU - Wyatt, Justin K.

AU - Warner, Philip M.

AU - Huber, Robert S.

AU - Li, Aiwen

AU - Kilgore, Michael W.

AU - Sticca, Robert P.

AU - Pollenz, Richard S.

PY - 2002/8/9

Y1 - 2002/8/9

N2 - Efficient routes to three classes of 10-membered oxa-enediynes are presented. The electronic and stereoelectronic contributions to half-lives are supported by density functional theory calculations. One member of this class cyclizes to give an isochroman which binds to and degrades the aryl hydrocarbon receptor (AhR).

AB - Efficient routes to three classes of 10-membered oxa-enediynes are presented. The electronic and stereoelectronic contributions to half-lives are supported by density functional theory calculations. One member of this class cyclizes to give an isochroman which binds to and degrades the aryl hydrocarbon receptor (AhR).

UR - http://www.scopus.com/inward/record.url?scp=0037047550&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037047550&partnerID=8YFLogxK

U2 - 10.1021/jo0256888

DO - 10.1021/jo0256888

M3 - Article

C2 - 12153275

AN - SCOPUS:0037047550

SN - 0022-3263

VL - 67

SP - 5727

EP - 5732

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 16

ER -

Oxa-enediynes: Probing the electronic and stereoelectronic contributions to the bergman cycloaromatization

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this