Total synthesis of the ammosamides

Citation:
Hughes, CC, Fenical W.  2010.  Total synthesis of the ammosamides. Journal of the American Chemical Society. 132:2528-2529.

Date Published:

Mar

Keywords:

agents, marine actinomycete, myosin

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.

Notes:

n/a

Website

DOI:

10.1021/ja9106572