Practical asymmetric synthesis of a selective endothelin A receptor (ETA) antagonist

Zhiguo J. Song; Matthew Zhao; Lisa Frey; Jing Li; Lushi Tan; Cheng Y. Chen; David M. Tschaen; Richard Tillyer; Edward J.J. Grabowski; Ralph Volante; Paul J. Reider; Yoshiaki Kato; Shigemitsu Okada; Takayuki Nemoto; Hiroki Sato; Atsushi Akao; Toshiaki Mase

doi:10.1021/ol016601s

Practical asymmetric synthesis of a selective endothelin A receptor (ETA) antagonist

Zhiguo J. Song, Matthew Zhao, Lisa Frey, Jing Li, Lushi Tan, Cheng Y. Chen, David M. Tschaen, Richard Tillyer, Edward J.J. Grabowski, Ralph Volante, Paul J. Reider, Yoshiaki Kato, Shigemitsu Okada, Takayuki Nemoto, Hiroki Sato, Atsushi Akao, Toshiaki Mase

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36 Scopus citations

Abstract

Equation presented A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide, and an aminophosphate-mediated sterospecific intramolecular enolate alkylation, which led to the formation of the five-membered ring bearing three contiguous asymmetric centers.

Original language	English (US)
Pages (from-to)	3357-3360
Number of pages	4
Journal	Organic letters
Volume	3
Issue number	21
DOIs	https://doi.org/10.1021/ol016601s
State	Published - Oct 18 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol016601s

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title = "Practical asymmetric synthesis of a selective endothelin A receptor (ETA) antagonist",

abstract = "Equation presented A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide, and an aminophosphate-mediated sterospecific intramolecular enolate alkylation, which led to the formation of the five-membered ring bearing three contiguous asymmetric centers.",

author = "Song, {Zhiguo J.} and Matthew Zhao and Lisa Frey and Jing Li and Lushi Tan and Chen, {Cheng Y.} and Tschaen, {David M.} and Richard Tillyer and Grabowski, {Edward J.J.} and Ralph Volante and Reider, {Paul J.} and Yoshiaki Kato and Shigemitsu Okada and Takayuki Nemoto and Hiroki Sato and Atsushi Akao and Toshiaki Mase",

year = "2001",

month = oct,

day = "18",

doi = "10.1021/ol016601s",

language = "English (US)",

volume = "3",

pages = "3357--3360",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

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TY - JOUR

T1 - Practical asymmetric synthesis of a selective endothelin A receptor (ETA) antagonist

AU - Song, Zhiguo J.

AU - Zhao, Matthew

AU - Frey, Lisa

AU - Li, Jing

AU - Tan, Lushi

AU - Chen, Cheng Y.

AU - Tschaen, David M.

AU - Tillyer, Richard

AU - Grabowski, Edward J.J.

AU - Volante, Ralph

AU - Reider, Paul J.

AU - Kato, Yoshiaki

AU - Okada, Shigemitsu

AU - Nemoto, Takayuki

AU - Sato, Hiroki

AU - Akao, Atsushi

AU - Mase, Toshiaki

PY - 2001/10/18

Y1 - 2001/10/18

N2 - Equation presented A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide, and an aminophosphate-mediated sterospecific intramolecular enolate alkylation, which led to the formation of the five-membered ring bearing three contiguous asymmetric centers.

AB - Equation presented A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide, and an aminophosphate-mediated sterospecific intramolecular enolate alkylation, which led to the formation of the five-membered ring bearing three contiguous asymmetric centers.

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U2 - 10.1021/ol016601s

DO - 10.1021/ol016601s

M3 - Article

C2 - 11594833

AN - SCOPUS:18044403182

SN - 1523-7060

VL - 3

SP - 3357

EP - 3360

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Practical asymmetric synthesis of a selective endothelin A receptor (ETA) antagonist

Abstract

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