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 o
Synthesis of casuarines [pentahydroxylated pyrrolizidines] by sodium hydrogen telluride-induced cyclisations of azidodimesylates
✍ Scribed by Andrew A. Bell; Lea Pickering; Alison A. Watson; Robert J. Nash; Yuan T. Pan; Alan D. Elbein; George W.J. Fleet
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 316 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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 me synmests ot sucn mgmy oxygenateo pyrrolizidiues.
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## Abstract (2E)‐α‐Amido‐α,β‐unsaturated sulfones, which are easily prepared by the condensation of α‐amido‐sulfones with aldehydes, can be desulfonylated by sodium hydrogen telluride to give (2Z)‐cinnamanilides with excellent stereoselectivity and in good yields.