Total Synthesis of (+)-Dibromophakellin

✍ Scribed by Takuya Imaoka; Osamu Iwamoto; Kei-ichi Noguchi; Kazuo Nagasawa

• Book ID: 101566550
• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 296 KB
• Volume: 48
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200806233

✦ Synopsis

Abstract

Two members of a family of pyrrole–imidazole marine alkaloids, (+)‐dibromophakellin and the nonnatural congener (+)‐phakellin, were synthesized enantioselectively from 4‐hydroxy‐L‐proline. The chiral aminal at C10 was constructed efficiently by means of an Overman‐type [3,3] sigmatropic rearrangement of an enamide (see scheme).magnified image