Total synthesis of the marine natural products lukianols A and B

Kaoru Takamura, Hisami Matsuo, Ayana Tanaka, Junji Tanaka, Tsutomu Fukuda, Fumito Ishibashi, Masatomo Iwao

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11 Citations (Scopus)

Abstract

Total synthesis of the pyrrolic marine natural products lukianols A (1) and B (2) has been achieved using N-benzenesulfonyl-3,4-dibromopyrrole (3) as a common starting material. The key synthetic strategy developed is the combined bromine-directed lithiation and palladium-catalyzed cross-coupling of 3 to produce 3,4-diarylpyrrol-2-carboxylates. Regioselective iodination of the phenolic intermediate 24 was thoroughly investigated for the synthesis of lukianol B.

Original languageEnglish
Pages (from-to)2782-2788
Number of pages7
JournalTetrahedron
Volume69
Issue number13
DOIs
Publication statusPublished - Apr 1 2013

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Takamura, K., Matsuo, H., Tanaka, A., Tanaka, J., Fukuda, T., Ishibashi, F., & Iwao, M. (2013). Total synthesis of the marine natural products lukianols A and B. Tetrahedron, 69(13), 2782-2788. https://doi.org/10.1016/j.tet.2013.01.077