THE INTRAMOLECULAR DIELS-ALDER REACTION WITH FURAN-DIENE - A NOVEL ROUTE TO (+/-)-GIBBERELLIN A5

被引：0

作者：

NUYTTENS, F

APPENDINO, G

DECLERCQ, PJ

机构：

来源：

SYNLETT | 1991年 / 07期

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D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel potential approach to 20-norgibberellins is described and exemplified with the total synthesis of (+/-)-gibberellin A5 from methyl (1S,2R,5S)-2-(2-furyl)-5-hydroxy-6-methylenebicyclo[3.2.1]octane-1-carboxylate. Key steps involve in intramolecular Diels-Alder reaction with the furan-diene moiety leading to a kaurenoid analogue and the subsequent ring contraction of the central 5-membered ring to yield the required carboxy-substituted cyclopentane moiety via a photochemical alpha-diazo ketone Wolff rearrangement.

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页码：526 / 528

页数：3

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