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

doi:10.1016/j.tet.2013.01.077

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

Department of Fundamental Organic Chemistry

Research output: Contribution to journal › Article › peer-review

20 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 language	English
Pages (from-to)	2782-2788
Number of pages	7
Journal	Tetrahedron
Volume	69
Issue number	13
DOIs	https://doi.org/10.1016/j.tet.2013.01.077
Publication status	Published - Apr 1 2013

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2013.01.077

Cite this

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title = "Total synthesis of the marine natural products lukianols A and B",

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.",

author = "Kaoru Takamura and Hisami Matsuo and Ayana Tanaka and Junji Tanaka and Tsutomu Fukuda and Fumito Ishibashi and Masatomo Iwao",

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doi = "10.1016/j.tet.2013.01.077",

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T1 - Total synthesis of the marine natural products lukianols A and B

AU - Takamura, Kaoru

AU - Matsuo, Hisami

AU - Tanaka, Ayana

AU - Tanaka, Junji

AU - Fukuda, Tsutomu

AU - Ishibashi, Fumito

AU - Iwao, Masatomo

N1 - Funding Information: This work was performed under the Cooperative Research Program of ‘Network Joint Research Center for Materials and Devices’ (Institute for Materials Chemistry and Engineering, Kyushu University).

PY - 2013/4/1

Y1 - 2013/4/1

N2 - 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.

AB - 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.

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Total synthesis of the marine natural products lukianols A and B

Abstract

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