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

80 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 - https://www.scopus.com/pages/publications/0035826378

UR - https://www.scopus.com/pages/publications/0035826378#tab=citedBy

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