Pyrrolidinones derived from (S)-pyroglutamic acid: Penmacric acid and analogues

Muhammed Anwar; Jonathan H. Bailey; Laura C. Dickinson; Hermia J. Edwards; Rajesh Goswami; Mark G. Moloney

doi:10.1039/b303924b

Pyrrolidinones derived from (S)-pyroglutamic acid: Penmacric acid and analogues

Muhammed Anwar
, Jonathan H. Bailey
, Laura C. Dickinson
, Hermia J. Edwards
, Rajesh Goswami
, Mark G. Moloney^*

^*Corresponding author for this work

University of Oxford

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

22 Citations (Scopus)

Abstract

Alkylation reactions using a-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.

Original language	English
Pages (from-to)	2364-2376
Number of pages	13
Journal	Organic and Biomolecular Chemistry
Volume	1
Issue number	13
DOIs	https://doi.org/10.1039/b303924b
Publication status	Published - 2003
Externally published	Yes

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10.1039/b303924b

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title = "Pyrrolidinones derived from (S)-pyroglutamic acid: Penmacric acid and analogues",

abstract = "Alkylation reactions using a-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.",

author = "Muhammed Anwar and Bailey, \{Jonathan H.\} and Dickinson, \{Laura C.\} and Edwards, \{Hermia J.\} and Rajesh Goswami and Moloney, \{Mark G.\}",

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journal = "Organic and Biomolecular Chemistry",

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T1 - Pyrrolidinones derived from (S)-pyroglutamic acid

T2 - Penmacric acid and analogues

AU - Anwar, Muhammed

AU - Bailey, Jonathan H.

AU - Dickinson, Laura C.

AU - Edwards, Hermia J.

AU - Goswami, Rajesh

AU - Moloney, Mark G.

PY - 2003

Y1 - 2003

N2 - Alkylation reactions using a-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.

AB - Alkylation reactions using a-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.

UR - https://www.scopus.com/pages/publications/0042808538

U2 - 10.1039/b303924b

DO - 10.1039/b303924b

M3 - Article

C2 - 12945710

AN - SCOPUS:0042808538

SN - 1477-0520

VL - 1

SP - 2364

EP - 2376

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 13

ER -

Pyrrolidinones derived from (S)-pyroglutamic acid: Penmacric acid and analogues

Abstract

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