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ChemInform Abstract: Synthesis of Casuarines (Pentahydroxylated Pyrrolizidines) by Sodium Hydrogen Telluride-Induced Cyclizations of Azidodimesylates.

✍ Scribed by A. A. BELL; L. PICKERING; A. A. WATSON; R. J. NASH; Y. T. PAN; A. D. ELBEIN; G. W. J. FLEET

Publisher: John Wiley and Sons
Year: 2010
Weight: 36 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199746222

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✦ Synopsis

Synthesis of Casuarines (Pentahydroxylated Pyrrolizidines) by Sodium Hydrogen Telluride-Induced Cyclizations of Azidodimesylates. -The first synthesis of diastereomers (cf. (IX); 4 examples) of the very highly functionalized alkaloid, casuarine (X), is reported. Key step is the efficient reduction of open chain azidodimesylates by sodium hydrogen telluride to allow the formation of the pyrrolizidine nucleus by bicyclization (cf. (VII) → (VIII)). -(BELL, A. A.;

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The ke]¢ ste~. in the slcn~esis of four ~te~.me~ of c.asuarine from eight carbon sugar laetones !s. me erttctent reo.ucaon o[ open c n~un azl.oodimesylates by sodium hydrogen ~ll~.de [Suz~'-T.~.oka reducuonlo~ aUow ~ rormauon, of the pyrroli~dine nucleus by oicyctisation. This ts me nrst report oz m