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  • Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation.

Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation.

Organic & biomolecular chemistry (2009-05-08)
Julien Ceccon, Grégory Danoun, Andrew E Greene, Jean-François Poisson
PMID19421437
ABSTRACT

An asymmetric synthesis of (+)-castanospermine is presented in which enol ether metathesis-hydroboration/oxidation is used for stereoselective installation of the trans-trans hydroxyl groups on the piperidine ring of the alkaloid.

MATERIALS
Product Number
Brand
Product Description
C3784
Sigma-Aldrich
Castanospermine, ≥94% (GC), BioUltra, from Castanospermum australe seeds
Pricing and availability is not currently available.
532673
Sigma-Aldrich
(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine, 98%
Pricing and availability is not currently available.