An intramolecular Tsuji-Trost reaction based approach to the synthesis of 6-methylene indolizidines

The efficient stereoselective preparation of C8 substituted indolizidines bearing a 6-methylene group, from the chiral pool starting material l-proline is reported. This synthesis, employing a Tsuji-Trost reaction as the key step, represents a potentially efficient route to pumiliotoxin natural prod...

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Bibliographic Details
Published in:Tetrahedron letters 2011-09, Vol.52 (38), p.4878-4881
Main Authors: Martin, Romy E., Polomska, Marta E., Byrne, Lindsay T., Stewart, Scott G.
Format: Article
Language:English
Subjects:
Allylation
Bearing
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indolizidines
Intramolecular Tsuji-Trost reaction
Natural products
Organic chemistry
Pools
Preparations and properties
Pumiliotoxins
Synthesis (chemistry)
Tetrahedrons
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Summary:The efficient stereoselective preparation of C8 substituted indolizidines bearing a 6-methylene group, from the chiral pool starting material l-proline is reported. This synthesis, employing a Tsuji-Trost reaction as the key step, represents a potentially efficient route to pumiliotoxin natural product epimers. Herein we describe the efficient stereoselective preparation of C8 substituted indolizidines bearing a 6-methylene group, from the chiral pool starting material l-proline. This synthesis, employing a Tsuji-Trost reaction as the key step, represents a potentially, efficient route to pumiliotoxin natural product epimers.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.07.047