First Total Synthesis of the Kikai Island Polybrominated C3'-N1 Bisindole Alkaloid by a Directed Metalation Strategy
Keisuke Tokushige1, Takumi Abe1
1Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Kita-ku, Okayama 7008530, Japan.
Abstract:
The first total synthesis of one out of four Kikai Island polybrominated C3'-N1 bisindole alkaloids from red alga Laurencia brongniartii is described. The key steps involve both dehydration of trans-hemiaminal and a C2'-methylthiolation of bisindole using dimethyl disulfide through directed metalation, followed by C3-methylthiolation using a N-SMe succinimide reagent.
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