American Chemical Society
ol4019453_si_001.pdf (2.4 MB)

The Exocyclic Olefin Geometry Control via Ireland–Claisen Rearrangement: Stereoselective Total Syntheses of Barmumycin and Limazepine E

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journal contribution
posted on 2013-09-06, 00:00 authored by Gints Smits, Ronalds Zemribo
Stereoselective total syntheses of Limazepine E and Barmumycin, potent, naturally occurring antitumor agents, are described. The total syntheses control the olefin geometry via a highly selective chelation-controlled Ireland–Claisen rearrangement of a seven-membered lactone-derived boron enolate for the synthesis of (E)-4-ethylidene proline, a crucial building block for a number of natural products.