由苯基甘氨醇衍生的δ-内酰胺对哌啶、中氮茚和喹嗪生物碱的对映选择性合成。

Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived delta-lactam.

作者信息

Amat Mercedes, Llor Núria, Hidalgo José, Escolano Carmen, Bosch Joan

机构信息

Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain.

出版信息

J Org Chem. 2003 Mar 7;68(5):1919-28. doi: 10.1021/jo0266083.

DOI:10.1021/jo0266083

PMID:12608811

Abstract

Starting from a common lactam, (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1), or its enantiomer, the enantioselective synthesis of 2-alkylpiperidines and cis- and trans-2,6-dialkylpiperidines is reported. The potential of this approach is illustrated by the synthesis of the piperidine alkaloids (R)-coniine, (2R,6S)-dihydropinidine, (2R,6R)-lupetidine, and (2R,6R)-solenopsin A, the indolizidine alkaloids (5R,8aR)-indolizidine 167B and (3R,5S,8aS)-monomorine I, and the nonnatural base (4R,9aS)-4-methylquinolizidine.

摘要

从一种常见的内酰胺（3R,8aS）-5-氧代-3-苯基-2,3,6,7,8,8a-六氢-5H-恶唑并[3,2-a]吡啶（1）或其对映体出发，报道了2-烷基哌啶以及顺式和反式2,6-二烷基哌啶的对映选择性合成。哌啶生物碱（R）-coniine、（2R,6S）-二氢哌啶、（2R,6R）-卢佩替啶和（2R,6R）-火蚁素A、吲哚里西啶生物碱（5R,8aR）-吲哚里西啶167B和（3R,5S,8aS）-单莫林I以及非天然碱（4R,9aS）-4-甲基喹嗪的合成展示了这种方法的潜力。