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Synthetic Studies of the Zoanthamine Alkaloids: Total Synthesis of Zoanthenol Based on an Isoaromatization Strategy
Author(s) -
Yoshimura Fumihiko,
Takahashi Yu,
Tanino Keiji,
Miyashita Masaaki
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000552
Subject(s) - total synthesis , ring (chemistry) , chemistry , platelet aggregation , hydrochloride , stereochemistry , combinatorial chemistry , organic chemistry , platelet , biology , immunology
The total synthesis of zoanthenol, a unique aromatic member of the zoanthamine alkaloids, which has exhibited potent anti‐platelet activities on human platelet aggregation, is described in full detail. The key step involves a Brønsted acid‐promoted isoaromatization in the AB ring system to install the crucial aromatic ring. We have not only succeeded in the first total synthesis of zoanthenol, but also established an alternative efficient synthetic route from the commercially available norzoanthamine hydrochloride to zoanthenol.