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ChemInform Abstract: Stereoselective Synthesis of (.+-.)-Indolizidines 167B and 209D and Their trans-Isomers Based on the Reductive Allylboration of Pyridine.

✍ Scribed by YU. N. BUBNOV; E. V. KLIMKINA; A. V. IGNATENKO

Publisher: John Wiley and Sons
Year: 2010
Weight: 38 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199837247

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✦ Synopsis

Stereoselective Synthesis of (±)-Indolizidines 167B and 209D and Their trans-Isomers Based on the Reductive Allylboration of Pyridine.

-A new and general method for the stereoselective synthesis of 5-substituted indolizidines based on the intramolecular cyclization of 2allyltetrahydropyridines, readily available from pyridine and triallylborane, is presented. Formation of the five-membered ring is achieved via a hydroborationoxidation-cyclization sequence. The efficiency of this method is demonstrated by the synthesis of the title indolizidine alkaloids (XIIa) and (X), resp., and their corresponding trans-isomers. -(BUBNOV,

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