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Total Synthesis of (+)‐Dibromophakellin |
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| Authors: | Takuya Imaoka Osamu Iwamoto Kei‐ichi Noguchi Dr. Kazuo Nagasawa Prof. Dr. |
| Affiliation: | Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology (TUAT), 2‐24‐16 Nakamachi, Koganei, Tokyo 184‐8588 (Japan), Fax: (+81)?42‐388‐7295 |
| 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).  |
| Keywords: | enamides marine natural products Overman rearrangement pyrrole– imidazole alkaloids total synthesis |