Total synthesis of the ammosamides.

Journal of the American Chemical Society
Chambers C Hughes, William Fenical

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.

References

Feb 5, 2005·Natural Product Reports·Edith M AntunesToufiek Samaai
Feb 10, 2006·Nature·Michael Famulok, Günter Mayer
Nov 17, 2006·Nature Chemical Biology·William Fenical, Paul R Jensen
Jul 23, 2008·Organic Letters·Gemma E VeitchSteven V Ley
Dec 19, 2008·Angewandte Chemie·Chambers C HughesWilliam Fenical
Dec 20, 2008·Angewandte Chemie·Chambers C HughesJames J La Clair
Jan 6, 2009·Nature Structural & Molecular Biology·Roman FedorovDietmar J Manstein
Jan 10, 2009·The Journal of Organic Chemistry·Hak Cheol KwonWilliam Fenical
May 9, 2009·Chemical Reviews·Gordon M CraggDavid J Newman

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Citations

Jun 3, 2010·Organic Letters·P V Narasimha ReddyMark Cushman
Jan 14, 2016·The Journal of Antibiotics·Takuji NakashimaSatoshi Ōmura
Mar 19, 2013·Biotechnology Advances·Saradavey Vinothkumar, P S Parameswaran
Jan 6, 2017·Journal of Natural Products·Daniela Reimer, Chambers C Hughes
Jan 21, 2016·Chemistry : a European Journal·Harekrishna SahooMahiuddin Baidya
Nov 9, 2017·Organic & Biomolecular Chemistry·Supravat SamantaSubbarayappa Adimurthy
Aug 3, 2010·Angewandte Chemie·Didier ZurwerraKarl-Heinz Altmann
Dec 24, 2011·Natural Product Reports·John W BluntMichèle R Prinsep
May 7, 2013·Natural Product Reports·Jonathan C Morris
Aug 2, 2019·Chemical & Pharmaceutical Bulletin·Mitsuhiro Arisawa
May 30, 2014·Natural Product Reports·Danielle Skropeta, Liangqian Wei
Sep 24, 2020·Chemical Communications : Chem Comm·Wei-Yu ShiYong-Min Liang
Jan 1, 2015·Chemistry of Heterocyclic Compounds·Lenar I MusinVladimir F Mironov
Aug 29, 2013·Organic & Biomolecular Chemistry·Ana G NeoCarlos F Marcos
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Cong WangShugeng Cao

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