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

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10.1021/ol006958g

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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)",

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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

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U2 - 10.1021/ol006958g

DO - 10.1021/ol006958g

M3 - Article

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SN - 1523-7060

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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

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