Total Synthesis of (+)-Dibromophakellin

Authors

  • Takuya Imaoka,

    1. 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
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  • Osamu Iwamoto,

    1. 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
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  • Kei-ichi Noguchi Dr.,

    1. 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
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  • Kazuo Nagasawa Prof. Dr.

    1. 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
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  • This research was supported financially in part by a Grant-in-Aid for Scientific Research (B) from JSPS (No. 20310130).

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).

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