First Total Synthesis of the Kikai Island Polybrominated C3′–N1 Bisindole Alkaloid by a Directed Metalation Strategy

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.

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Natural Products, copyright © 2025 American Chemical Society and American Society of Pharmacognosy after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.jnatprod.5c01131.

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