One-Step Preparation of Pyrrolo[1,4]benzodiazepine Dilactams: Total Synthesis of Oxoprothracarcin, Boseongazepines B and C

A one-step synthesis of pyrrolo[1,4]benzodiazepine dilactams has been developed. The high yielding method involves direct coupling of unprotected anthranilic acids with proline esters. This transformation was successfully applied in the first total syntheses of boseongazepines B and C as well as oxoprothracarcin and limazepine E

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

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

The Exocyclic Olefin Geometry Control via Ireland—Claisen Rearrangement: Stereoselective Total Syntheses of Barmumycin (V) and Limazepine E (VI)

The highly selective Ireland—Claisen rearrangement of seven-membered lactone-derived boron enolate generated in situ is the key step to synthesize the naturally occurring antitumor agents (V) and (VI)

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

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 (<i>E</i>)-4-ethylidene proline, a crucial building block for a number of natural products