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ChemInform Abstract: 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.

✍ Scribed by Simon J. F. Macdonald; Keith Mills; Julie E. Spooner; Richard J. Upton; Michael D. Dowle

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

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✦ Synopsis

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 (VII) is presented.

-(MACDONALD, SIMON J. F.;

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of (.+-.)
ChemInform Abstract: Synthesis of (.+-.)-Oxohexahydrofuro[3,2-b]pyrroles (Pyrrolidine-trans-lactones) via a Reduction—Alkylation Protocol.
✍ Simon J. F. Macdonald; John G. Montana; Doreen M. Buckley; Michael D. Dowle 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

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