Synthesis of β-hydroxypiperidine alkaloids by anodic oxidation of carbamates and hydroboration
作者:
Mark Plehiers,
Claude Hootelé,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1996)
卷期:
Volume 74,
issue 12
页码: 2444-2453
ISSN:0008-4042
年代: 1996
DOI:10.1139/v96-273
出版商: NRC Research Press
数据来源: NRC
摘要:
The β-hydroxypiperidine alkaloids (±)-pseudoconhydrine, (±)-N-methylpseudoconhydrine, (−)-5-hydroxysedamine, and (+)-sedacryptine were synthesized. Successive functionalization of the piperidine ring via anodic methoxylation allowed the regio- and stereoselective introduction of the substituents. The α and α′ substituents were introduced by application of the sequence elimination–nucleophilic addition from 2- or 2,5-substituted 6-methoxycarbamates. Hydroboration – oxidation of enecarbamates, obtained by elimination of methanol from α-methoxycarbamates, allowed the introduction of the β-hydroxy function.Keywords: alkaloid, Sedum,N-acyliminium, enecarbamate.
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