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A concise and efficient synthesis of (-)-allosamizoline.

Abstract:
A regio- and stereocontrolled total synthesis of (-)-allosamizoline is described. The key steps for this synthesis are ring-closing metathesis to form the cyclopentene core, halocyclization to afford the oxazoline ring, and finally stereoselective alkene radical addition followed by an alkene isomerization reaction to install the hydroxymethyl group. (-)-Allosamizoline was prepared in a total of 13 steps and 22% overall yield.

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Publisher copy:
10.1021/ol702449m

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Organic letters
Volume:
9
Issue:
26
Pages:
5509-5511
Publication date:
2007-12-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:b5bdb507-de48-4ab1-9a86-fa6858648f03
Source identifiers:
34048
Local pid:
pubs:34048
Language:
English
Keywords:

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