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Polyhydroxylated indolizidine alkaloids—an efficient synthesis of 1-deoxy-8,8a-di-epi-castanospermine

✍ Scribed by Ari M.P Koskinen; Oili A Kallatsa

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
284 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 choice of reaction conditions, the approach can also be applied in selective preparation of several isomers of deoxycastanospermine. The length (9 steps) and overall yield of the title compound trihydroxyindolidine 1, 7.3%, compares well with the literature syntheses of similar compounds.

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Enantiomeric synthesis of polyhydroxylated indolizidine analogues related to castanospermine: 1-deoxy-7-epicastanospermine and 1,7-dideoxy-7-fluorocastanospermine
✍ C.-Kuan Lee; K.Y. Sim; Jun Zhu 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 309 KB

Trihydroxyindolizidine (1) and its (7R)-deoxyfh~on~ analogue (2) was synthesised from 5,8-benzyloxycarbonylimino-5.6,7,8-tetradeoxy-l,2-0-isopropylidene-a-D-gluco-octose (3). The key step is an oxidation-reduction sequence. Introduction of a fluoro substituent at C-3 (6) was readily effected by disp