Synthesis of (Β±)-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
ChemInform Abstract: Synthesis of (.+-.)-Oxohexahydrofuro[3,2-b]pyrroles (Pyrrolidine-trans-lactones) Using Acyl-Iminium Chemistry.
β Scribed by Simon J. F. Macdonald; Julie E. Spooner; Michael D. Dowle
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 36 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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A Stereoselective Synthesis via a 5-exo-trig Cyclization of trans-2-Oxohexahydro-2H-furo[3,2-b]pyrroles (Pyrrolidine-trans-lactones) -Potent, Novel Elastase Inhibitors. -With the title cyclization to (VI) as the key step, a stereoselective approach to a potent human neutrophile elastase inhibitor (
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## Abstract The cyclization of substrates (I) with aldehydes is promoted by Fe(III)βsalts to yield pyrrolidines (III) after reductive workβup.