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Application of the diastereoselective photodeconjugation of ?,?-unsaturated esters to the synthesis of gymnastatin H.

ABSTRACT: The asymmetric synthesis of gymnastatin H has been achieved by using the photoisomerisation of a conjugated ester to its ?,?-unsaturated isomer through the protonation of a in situ generated dienol as key step. Thanks to diacetone D-glucose used as a chiral alkoxy group, the protonation occurred well onto one of the two diastereotopic faces with very high yields and selectivities. Moreover, by this way the configuration of the C-6 centre of the target molecule was controlled.

SUBMITTER: Raffier L

PROVIDER: S-EPMC3064449 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H.

Raffier Ludovic L Piva Olivier O

Beilstein journal of organic chemistry 20110202

The asymmetric synthesis of gymnastatin H has been achieved by using the photoisomerisation of a conjugated ester to its β,γ-unsaturated isomer through the protonation of a in situ generated dienol as key step. Thanks to diacetone D-glucose used as a chiral alkoxy group, the protonation occurred well onto one of the two diastereotopic faces with very high yields and selectivities. Moreover, by this way the configuration of the C-6 centre of the target molecule was controlled. ...[more]

PMID: 21448437

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