Stereoselective approaches to 2,3,6-trisubstituted piperidines. An enantiospecific synthesis of quinolizidine (-)-217A

The enantiospecific and diastereocontrolled total synthesis of alkaloid (-)-217A is described that employs a stepwise [3+3] annelation strategy and a piperidine 2,3-cyclopropanation-ring opening reaction as the key steps.

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2011-09, Vol.47 (35), p.9804-9806
Main Authors: Mancey, Nicole C, Sandon, Nicolas, Auvinet, Anne-Laure, Butlin, Roger J, Czechtizky, Werngard, Harrity, Joseph P A
Format: Article
Language:English
Subjects:
Alkaloids
Cyclopropanes - chemistry
Piperidine
Piperidines - chemical synthesis
Piperidines - chemistry
Quinolizines - chemical synthesis
Quinolizines - chemistry
Stereoisomerism
Strategy
Substrate Specificity
Synthesis
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Description
Summary:The enantiospecific and diastereocontrolled total synthesis of alkaloid (-)-217A is described that employs a stepwise [3+3] annelation strategy and a piperidine 2,3-cyclopropanation-ring opening reaction as the key steps.
ISSN:1359-7345
1364-548X
DOI:10.1039/c1cc13048j