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Total synthesis of the ammosamides.


ABSTRACT: The ammosamides A-C are chlorinated pyrrolo[4,3,2-de]quinoline metabolites isolated from the marine-derived Streptomyces strain CNR-698. The natural products, which possess a dense array of heteroatoms, were synthesized in 17-19 steps from 4-chloroisatin. That the five nitrogen atoms were introduced at the appropriate time and in a suitable oxidation state was key to the success of the total synthesis. Compared to synthetic deschloro ammosamide B, natural ammosamide B is much less susceptible to oxidative degradation.

SUBMITTER: Hughes CC 

PROVIDER: S-EPMC2828514 | BioStudies | 2010-01-01

REPOSITORIES: biostudies

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