Total synthesis of the marine natural products lukianols A and B

TETRAHEDRON

卷:69

Article

Takamura, Kaoru¹  Matsuo, Hisami¹  Tanaka, Ayana¹  Tanaka, Junji²  Fukuda, Tsutomu¹  Ishibashi, Fumito³  Iwao, Masatomo¹ 

[1] Nagasaki Univ, Grad Sch Engn, Nagasaki 8528521, Japan

[2] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan

[3] Nagasaki Univ, Grad Sch Fisheries Sci & Environm Studies, Nagasaki 8528521, Japan

关键词: Lukianols A, B;    Total synthesis;    Pyrrole;    Directed lithiation;    Cross-coupling;   

DOI  :  10.1016/j.tet.2013.01.077

来源: Elsevier

【 摘 要 】

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. (C) 2013 Published by Elsevier Ltd.

【 授权许可】

Free