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

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 wel...

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Main Authors:	Ludovic Raffier, Olivier Piva
Format:	Article
Language:	English
Published:	Beilstein-Institut 2011-02-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	amide diastereoselective protonation dienol isomerisation Wittig reaction
Online Access:	https://doi.org/10.3762/bjoc.7.21

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spelling	doaj-4c5101678cbf4bde88c9ecb050830dcc2021-02-02T00:16:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-02-017115115510.3762/bjoc.7.211860-5397-7-21Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin HLudovic Raffier0Olivier Piva1Université Lyon 1, UMR 5246 CNRS, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire, 69622 Villeurbanne, FranceUniversité Lyon 1, UMR 5246 CNRS, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire, 69622 Villeurbanne, FranceThe 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.https://doi.org/10.3762/bjoc.7.21amidediastereoselective protonationdienolisomerisationWittig reaction
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Ludovic Raffier Olivier Piva
spellingShingle	Ludovic Raffier Olivier Piva Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H Beilstein Journal of Organic Chemistry amide diastereoselective protonation dienol isomerisation Wittig reaction
author_facet	Ludovic Raffier Olivier Piva
author_sort	Ludovic Raffier
title	Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H
title_short	Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H
title_full	Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H
title_fullStr	Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H
title_full_unstemmed	Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H
title_sort	application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin h
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2011-02-01
description	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.
topic	amide diastereoselective protonation dienol isomerisation Wittig reaction
url	https://doi.org/10.3762/bjoc.7.21
work_keys_str_mv	AT ludovicraffier applicationofthediastereoselectivephotodeconjugationofabunsaturatedesterstothesynthesisofgymnastatinh AT olivierpiva applicationofthediastereoselectivephotodeconjugationofabunsaturatedesterstothesynthesisofgymnastatinh
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Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H

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