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ChemInform Abstract: Synthesis of (.+-.)-Oxohexahydrofuro[3,2-b]pyrroles (Pyrrolidine-trans-lactones) via a Reduction—Alkylation Protocol.

✍ Scribed by Simon J. F. Macdonald; John G. Montana; Doreen M. Buckley; Michael D. Dowle

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of (±)-Oxohexahydrofuro [3,2-b]pyrroles (Pyrrolidine-translactones) via a Reduction-Alkylation Protocol. -Hydride reduction of the cyclic keto-ester (I) gives mainly the cis-lactone (II). However, immediate hydroxyl inversion with benzoic acid prior to lactonization gives the trans-product (V), thus providing a route for the synthesis of the pyrrolidinetrans-lactone (XI). -(MACDONALD, SIMON

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