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Alkene ozonolysis in the presence of diazo functionality: accessing an intermediate for squalestatin synthesis

Abstract:
Studies on both the propensity for intramolecular cycloaddition between diazo and alkene functionality, and the tolerance of α-substituted α-diazoesters towards ozone in the presence of an alkene, led to chemoselective alkene ozonolysis of an ε-unsaturated-α-diazoester to give a key racemic diazoketone for the synthesis of 6,7-dideoxysqualestatin H5.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1055/s-0039-1690180

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Oriel College
Role:
Author
Publisher:
Thieme Gruppe
Journal:
Synthesis More from this journal
Volume:
51
Issue:
22
Pages:
4231-4238
Publication date:
2019-09-13
Acceptance date:
2019-07-26
DOI:
EISSN:
1437-210X
ISSN:
0039-7881
Language:
English
Keywords:
Pubs id:
pubs:1053917
UUID:
uuid:07a488bf-0e53-40b3-80bb-49442e72287b
Local pid:
pubs:1053917
Source identifiers:
1053917
Deposit date:
2019-09-17

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