期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 7, 期 -, 页码 151-155出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.21
关键词
amide; diastereoselective protonation; dienol; isomerisation; Wittig reaction
资金
- Ministere de l'Enseignement Superieur et de la Recherche
- Universite Lyon 1
- CNRS
- Region Rhone-Alpes
The asymmetric synthesis of gymnastatin H has been achieved by using the photoisomerisation of a conjugated ester to its beta,gamma-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.
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