A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists

Debra J. Wallace; Jonathan M. Goodman; Derek J. Kennedy; Antony J. Davies; Cameron J. Cowden; Michael S. Ashwood; Ian F. Cottrell; Ulf H. Dolling; Paul J. Reider

doi:10.1021/ol006958g

A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists

Debra J. Wallace, Jonathan M. Goodman, Derek J. Kennedy, Antony J. Davies, Cameron J. Cowden, Michael S. Ashwood, Ian F. Cottrell, Ulf H. Dolling, Paul J. Reider

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

77 Scopus citations

Abstract

Equation presented The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing matathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.

Original language	English (US)
Pages (from-to)	671-674
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	5
DOIs	https://doi.org/10.1021/ol006958g
State	Published - Mar 8 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol006958g

Cite this

@article{44f6daa957f64c48948d64ce6701b3d9,

title = "A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists",

abstract = "Equation presented The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing matathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.",

author = "Wallace, {Debra J.} and Goodman, {Jonathan M.} and Kennedy, {Derek J.} and Davies, {Antony J.} and Cowden, {Cameron J.} and Ashwood, {Michael S.} and Cottrell, {Ian F.} and Dolling, {Ulf H.} and Reider, {Paul J.}",

year = "2001",

month = mar,

day = "8",

doi = "10.1021/ol006958g",

language = "English (US)",

volume = "3",

pages = "671--674",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists

AU - Wallace, Debra J.

AU - Goodman, Jonathan M.

AU - Kennedy, Derek J.

AU - Davies, Antony J.

AU - Cowden, Cameron J.

AU - Ashwood, Michael S.

AU - Cottrell, Ian F.

AU - Dolling, Ulf H.

AU - Reider, Paul J.

PY - 2001/3/8

Y1 - 2001/3/8

N2 - Equation presented The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing matathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.

AB - Equation presented The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing matathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.

UR - http://www.scopus.com/inward/record.url?scp=0035826378&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035826378&partnerID=8YFLogxK

U2 - 10.1021/ol006958g

DO - 10.1021/ol006958g

M3 - Article

C2 - 11259033

AN - SCOPUS:0035826378

SN - 1523-7060

VL - 3

SP - 671

EP - 674

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this