Synthesis of quinolizidines and indolizidines via an intramolecular Mannich reaction
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 447-453
- https://doi.org/10.1039/p19860000447
Abstract
Acid treatment of the addition products (13) of an aminopentanal or aminobutanal diethyl acetal and an α,β-unsaturated ketone gave the quinolizidin-2-ones (11), (12), (20), (36), and (37) and the indolizidin-7-ones (9), (10), (16)–(19), (34), and (35) respectively. The ratios of stereoisomers obtained were rationalised by a consideration of the relative stabilities of the transition states and the effect of steric hindrance in the Mannich cyclisation.This publication has 3 references indexed in Scilit:
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- Pyrrolizidine alkaloids: evidence for the involvement of spermidine and spermine in the biosynthesis of retronecineJournal of the Chemical Society, Chemical Communications, 1979
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