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Utility of the ammonia-free Birch reduction of electron-deficient pyrroles: total synthesis of the 20s proteasome inhibitor, clasto-lactacystin beta-lactone.

Abstract:

A new synthesis of the 20S proteasome inhibitor clasto-lactacystin beta-lactone is described. Our route to this important natural product involves the partial reduction of an electron deficient pyrrole as a key step. By judicious choice of enolate counterion, we were able to exert complete control over the stereoselectivity of the reduction/aldol reaction. Early attempts to complete the synthesis by using a C-4 methyl substituted pyrrole are described in full, together with our attempts to pr...

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Publication status:
Published

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Publisher copy:
10.1002/chem.200401119

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Journal:
Chemistry (Weinheim an der Bergstrasse, Germany)
Volume:
11
Issue:
14
Pages:
4227-4238
Publication date:
2005-07-01
DOI:
EISSN:
1521-3765
ISSN:
0947-6539
Source identifiers:
33080
Language:
English
Keywords:
Pubs id:
pubs:33080
UUID:
uuid:6ea691fe-f3ec-4220-8452-3f52e97c8cf7
Local pid:
pubs:33080
Deposit date:
2012-12-19

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