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

Organic Letters 2013
Gints Šmits, Rolands 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.

Keywords
alkene; antineoplastic agent; azepine derivative; barmumycin; limazepine E; pyrrolidine derivative
DOI
10.1021/ol4019453
Hyperlink
http://pubs.acs.org/doi/abs/10.1021/ol4019453

Šmits, G., Zemribo, R. The Exocyclic Olefin Geometry Control via Ireland–Claisen Rearrangement: Stereoselective Total Syntheses of Barmumycin and Limazepine E. Organic Letters, 2013, Vol.15, Iss.17, pp.4406-4409. ISSN 1523-7060. e-ISSN 1523-7052. Available from: doi:10.1021/ol4019453

Publication language
English (en)