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Asymmetric synthesis of a highly functionalized beta-amino acid: the key amino acid of sperabillins B and D

Abstract:
The asymmetric synthesis of the highly functionalized (3R,5R,6R)-3,6-diamino-5-hydroxyheptanoic acid, the key amino acid fragment of sperabillins B and D, was achieved by an asymmetric Michael addition of lithium (R)-(α-methylbenzyl)allylamide 10 to (E,E)-2,5-heptadienoate establishing the C-3 stereogenic centre, the information from which was propagated to the C-5 and C-6 centres by a highly stereoselective iodocyclocarbamation reaction.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Ichihara, O More by this author
Journal:
TETRAHEDRON LETTERS
Volume:
40
Issue:
52
Pages:
9313-9316
Publication date:
1999-12-24
DOI:
ISSN:
0040-4039
URN:
uuid:2425d624-7cec-4548-84b5-30c2d6fe9e4c
Source identifiers:
110613
Local pid:
pubs:110613
Language:
English

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