title: The exocyclic olefin geometry control via Ireland-Claisen rearrangement: stereoselective total syntheses of Barmumycin and Limazepine E.
abstract: 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.
authors: Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.
authors: Gints
authors: G
authors: Smits
authors: Ronalds
authors: R
authors: Zemribo
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000970:Antineoplastic Agents; D001381:Azepines; D011759:Pyrrolidines; C556253:barmumycin; C586351:limazepine E