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Asymmetric routes towards polyfunctionalized pyrrolidines: application to the synthesis of alkaloid analogues

✍ Scribed by Martial Toffano; Bruno Dudot; Anne Zaparucha; Jacques Royer; Mireille Sevrin; Pascal George; Angèle Chiaroni

Book ID
104360052
Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
268 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

The Mukaiyama aldol type condensation of t-butyldimethylsilyloxypyrrole 1b with methyl 2-formylbenzoate furnished the aldol adduct 9 with high yield and complete stereoselectivity. An erythro (anti) configuration was established (X-ray) in sharp contrast with the reaction of 1b with aliphatic aldehydes. Simple chemical transformations were used to transform 9 into original phthalidopyrrolidine compound analogous of bicuculline alkaloids.

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ChemInform Abstract: Asymmetric Routes T
ChemInform Abstract: Asymmetric Routes Towards Polyfunctionalized Pyrrolidines: A Short Diastereoselective Synthesis of Polyhydroxylated Pyrrolidines and an Indolizidine.
✍ Bruno Dudot; Laurent Micouin; Isabelle Baussanne; Jacques Royer 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

Starting from the (R)-(-)-phenylglycinol derivative (I), the stereoselective synthesis of polyhydroxylated pyrrolidines [cf. (VIII)] and the indolizidine (XII) is based on the diastereoselective condensation of the chiral silyloxypyrrole (III) with aldehydes (IV). The preparation of the indolizidine