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Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine.

Abstract:
The highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C (41% yield over 8 steps), N,O,O-triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps).
Publication status:
Published

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Publisher copy:
10.1039/b801357h

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Journal:
Organic and biomolecular chemistry
Volume:
6
Issue:
9
Pages:
1655-1664
Publication date:
2008-05-01
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Source identifiers:
110560
Language:
English
Keywords:
Pubs id:
pubs:110560
UUID:
uuid:cfb42e87-79aa-4cb6-aef2-f6d8c66c4470
Local pid:
pubs:110560
Deposit date:
2012-12-19

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