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New syntheses of two epimers of (+)-castanospermine: (+)-8a-Epi- and (+)-1,8a-Di-epi-castanospermine

✍ Scribed by Ewa Bartnicka; Aleksander Zamojski


Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
766 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis


Two epimers of (+)-castanospermine, (IS.&~.7R.SR,g~S).l,6,7.8-tetrahydroxyindolizJdine l(+)-8a-epi-castanosperminel (4) and (IR,6S.7R.SR,Se/~) derivative [(+)-l,8a-di-epi-eastanospermine]

(5) were synthesized from methyl c~-D-glucopyranoside.


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✍ Ari M.P Koskinen; Oili A Kallatsa πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 284 KB

A new and efficient enantioselective total synthesis of the title deoxycastanospermine derivative has been developed, based on amino acid and b-ketophosphonate chemistry, as well as employment of internal asymmetric induction for the creation of the new chiral centers proved successful. With proper