A practical synthesis for the core structure of a family of selective prostaglandin D2 receptor antagonists

Kevin R. Campos; Michel Journet; Dongwei Cai; Jason J. Kowal; Sandra Lee; Robert D. Larsen; Paul J. Reider

doi:10.1021/jo026511g

A practical synthesis for the core structure of a family of selective prostaglandin D₂ receptor antagonists

Kevin R. Campos, Michel Journet, Dongwei Cai, Jason J. Kowal, Sandra Lee, Robert D. Larsen, Paul J. Reider

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

11 Scopus citations

Abstract

A convergent synthesis was developed for the production of the core structure of prostaglandin D₂ receptor antagonists for the treatment of allergic rhinitis. The key steps in this synthesis were a highly diastereoselective alkylation of (+)-nopinone, a chemo- and stereoselective reduction of an oxime to an amine, and a well-controlled reduction of an aminoalkyne to a (Z)-olefin.

Original language	English (US)
Pages (from-to)	2338-2342
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	68
Issue number	6
DOIs	https://doi.org/10.1021/jo026511g
State	Published - Mar 21 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo026511g

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abstract = "A convergent synthesis was developed for the production of the core structure of prostaglandin D2 receptor antagonists for the treatment of allergic rhinitis. The key steps in this synthesis were a highly diastereoselective alkylation of (+)-nopinone, a chemo- and stereoselective reduction of an oxime to an amine, and a well-controlled reduction of an aminoalkyne to a (Z)-olefin.",

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AU - Campos, Kevin R.

AU - Journet, Michel

AU - Cai, Dongwei

AU - Kowal, Jason J.

AU - Lee, Sandra

AU - Larsen, Robert D.

AU - Reider, Paul J.

PY - 2003/3/21

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AB - A convergent synthesis was developed for the production of the core structure of prostaglandin D2 receptor antagonists for the treatment of allergic rhinitis. The key steps in this synthesis were a highly diastereoselective alkylation of (+)-nopinone, a chemo- and stereoselective reduction of an oxime to an amine, and a well-controlled reduction of an aminoalkyne to a (Z)-olefin.

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IS - 6

ER -

A practical synthesis for the core structure of a family of selective prostaglandin D₂ receptor antagonists

Abstract

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