Practical route to a new class of LTD4 receptor antagonists

Robert D. Larsen; Edward G. Corley; Anthony O. King; James D. Carroll; Paul Davis; Thomas R. Verhoeven; Paul J. Reider; Marc Labelle; Jacques Y. Gauthier; Yi Bin Xiang; Robert J. Zamboni

doi:10.1021/jo952103j

Practical route to a new class of LTD₄ receptor antagonists

Robert D. Larsen, Edward G. Corley, Anthony O. King, James D. Carroll, Paul Davis, Thomas R. Verhoeven, Paul J. Reider, Marc Labelle, Jacques Y. Gauthier, Yi Bin Xiang, Robert J. Zamboni

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

252 Scopus citations

Abstract

A general approach to the synthesis of a new class of LTD₄ antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.

Original language	English (US)
Pages (from-to)	3398-3405
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	61
Issue number	10
DOIs	https://doi.org/10.1021/jo952103j
State	Published - May 17 1996
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo952103j

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title = "Practical route to a new class of LTD4 receptor antagonists",

abstract = "A general approach to the synthesis of a new class of LTD4 antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.",

author = "Larsen, {Robert D.} and Corley, {Edward G.} and King, {Anthony O.} and Carroll, {James D.} and Paul Davis and Verhoeven, {Thomas R.} and Reider, {Paul J.} and Marc Labelle and Gauthier, {Jacques Y.} and Xiang, {Yi Bin} and Zamboni, {Robert J.}",

year = "1996",

month = may,

day = "17",

doi = "10.1021/jo952103j",

language = "English (US)",

volume = "61",

pages = "3398--3405",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Practical route to a new class of LTD4 receptor antagonists

AU - Larsen, Robert D.

AU - Corley, Edward G.

AU - King, Anthony O.

AU - Carroll, James D.

AU - Davis, Paul

AU - Verhoeven, Thomas R.

AU - Reider, Paul J.

AU - Labelle, Marc

AU - Gauthier, Jacques Y.

AU - Xiang, Yi Bin

AU - Zamboni, Robert J.

PY - 1996/5/17

Y1 - 1996/5/17

N2 - A general approach to the synthesis of a new class of LTD4 antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.

AB - A general approach to the synthesis of a new class of LTD4 antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.

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U2 - 10.1021/jo952103j

DO - 10.1021/jo952103j

M3 - Article

AN - SCOPUS:15844376844

SN - 0022-3263

VL - 61

SP - 3398

EP - 3405

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 10

ER -

Practical route to a new class of LTD₄ receptor antagonists

Abstract

All Science Journal Classification (ASJC) codes

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