The Preparation of (−)-Grandisine B from (+)-Grandisine D; A Biomimetic Total Synthesis or Formation of an Isolation Artefact?

An efficient new alkyne-acetal cyclization procedure has been developed to prepare enantiopure indolizidine building blocks from l-proline and then applied to prepare the Elaeocarpus-derived alkaloids grandisine B and grandisine D in an efficient manner. However, evidence is presented which indicate...

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Bibliographic Details
Published in:Organic letters 2011-08, Vol.13 (15), p.3976-3979
Main Authors: Cuthbertson, James D, Godfrey, Andrew A, Taylor, Richard J. K
Format: Article
Language:English
Subjects:
Biomimetic Materials - chemical synthesis
Biomimetic Materials - isolation & purification
Cyclization
Indolizines - chemical synthesis
Indolizines - isolation & purification
Models, Molecular
Molecular Structure
Stereoisomerism
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Summary:An efficient new alkyne-acetal cyclization procedure has been developed to prepare enantiopure indolizidine building blocks from l-proline and then applied to prepare the Elaeocarpus-derived alkaloids grandisine B and grandisine D in an efficient manner. However, evidence is presented which indicates that grandisine B does not occur naturally but is formed by reaction of grandisine D with ammonia during the extraction/purification process.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2014939