ChemInform Abstract: Asymmetric Routes Towards Polyfunctionalized Pyrrolidines: A Short Diastereoselective Synthesis of Polyhydroxylated Pyrrolidines and an Indolizidine.

✍ Scribed by Bruno Dudot; Laurent Micouin; Isabelle Baussanne; Jacques Royer

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199931138

✦ Synopsis

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 (XII) represents a formal total synthesis of (-)-8a-epi-swainsonine.