Syntheses of ficuseptine, juliprosine, and juliprosopine by biomimetic intramolecular Chichibabin pyridine syntheses

被引：43

作者：

Snider, BB ^{[1
]}

Neubert, BJ ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem MS 015, Waltham, MA 02454 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol050931l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Biomimetic intramolecular Chichibabin pyridine syntheses using two molecules of an aldehyde and 4-aminobutanal dimethyl acetal (6) proceed efficiently in AcOH at 95 degrees C to give 2,3-dihydro-1H-indolizinium salts. Reaction occurs at 25 degrees C if 1-pyrroline (5) is used instead of 6. This reaction has been used for a one-step synthesis of ficuseptine (1) and the first syntheses of juliprosine (2) and juliprosopine (17t), which is now assigned as the trans stereoisomer.

引用

页码：2715 / 2718

页数：4

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