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

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 stere...

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Autores principales: Davies, S, Ichihara, O
Formato: Journal article
Lenguaje:English
Publicado: 1999
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author Davies, S
Ichihara, O
author_facet Davies, S
Ichihara, O
author_sort Davies, S
collection OXFORD
description 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.
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spelling oxford-uuid:2425d624-7cec-4548-84b5-30c2d6fe9e4c2022-03-26T11:48:22ZAsymmetric synthesis of a highly functionalized beta-amino acid: the key amino acid of sperabillins B and DJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2425d624-7cec-4548-84b5-30c2d6fe9e4cEnglishSymplectic Elements at Oxford1999Davies, SIchihara, OThe 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.
spellingShingle Davies, S
Ichihara, O
Asymmetric synthesis of a highly functionalized beta-amino acid: the key amino acid of sperabillins B and D
title Asymmetric synthesis of a highly functionalized beta-amino acid: the key amino acid of sperabillins B and D
title_full Asymmetric synthesis of a highly functionalized beta-amino acid: the key amino acid of sperabillins B and D
title_fullStr Asymmetric synthesis of a highly functionalized beta-amino acid: the key amino acid of sperabillins B and D
title_full_unstemmed Asymmetric synthesis of a highly functionalized beta-amino acid: the key amino acid of sperabillins B and D
title_short Asymmetric synthesis of a highly functionalized beta-amino acid: the key amino acid of sperabillins B and D
title_sort asymmetric synthesis of a highly functionalized beta amino acid the key amino acid of sperabillins b and d
work_keys_str_mv AT daviess asymmetricsynthesisofahighlyfunctionalizedbetaaminoacidthekeyaminoacidofsperabillinsbandd
AT ichiharao asymmetricsynthesisofahighlyfunctionalizedbetaaminoacidthekeyaminoacidofsperabillinsbandd