Asymmetric synthesis of a highly functionalized β-amino acid: the key amino acid of sperabillins B and D |
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Authors: | Stephen G Davies Osamu Ichihara |
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Institution: | aThe Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY, UK |
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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)-(-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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