Total syntheses of natural (+)-sesbanimide A and (−)-sesbanimide B

✍ Scribed by Fuyuhiko Matsuda; Shiro Terashima

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 255 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84808-x

✦ Synopsis

Natural (+)-sesbanimide A (l) and (-)-sesbanimide B ($, potent antitumor alkaloids, were efficiently synthesized from the (-)-glutarimide diol ($, corresponding to the AB-ring system of l and &, which had already been derived from readily available D-xylose. Our total synthesis obviously established the absolute configuration of l. Potent antitumor alkaloids, sesbanimide A (A) and B (4) were isolated from the seeds of the leguminous plant, Sesbania drummondii. They have shown notable cytotoxicity against KB cells in vitro, and potent inhibitory activity against P388 murine leukemia in vivo. 1 These -compounds have unique tricyclic structures in which the three rings are linkedbythetwo single bonds. These remarkable antitumor activity and novel structures distinguished these molecules as unusually attractivetargetsfor total synthesis. 2 Previously, we had reported an efficient synthesis of the (-)-glutarimide dip1 ($), corresponding to the AB-ring system of ,J, and 4, from readily available D-xylose.3

In this communication we would like to report on the first total syntheses of natural (+)-sesbanimide A (J,