Of -nanaomycin

This reaction is applied to the intramolecular regioselective cyclization of the 3-alkoxybenzoeyelobutenedione 60 to 61, a precursor of nanaomycin A 62 [33], (Scheme 23)... 

This regioselective synthesis of benzannelated rings, which, unlike its Friedel Crafts equivalent, is not perturbed by the nature of other directing groups carried by the ring, has been used in several syntheses. Indanone 76 from cyclisation of 75 is an intermediate in a synthesis of nanaomycin A,44 and tetralone 77 is an intermediate in a synthetic study towards daunomycin 45... 

Pyranonaphthoquinones. The reaction of phthaloylmetal complexes with alkynes to give naphthoquinones (10, 221-222) has been extended to a synthesis of pyrano-naphthoquinones. An intramolecular version of the reaction is used to control the regio-selectivity. The method is outlined in Scheme (1) for a synthesis of nanaomycin (6) and the cw-epimer (7). 

The effects of ammonium ion on the production of the benzoisochromane quinone antibiotic nanaomycin was studied using Streptomyces rosa [106]. Additions of small amounts (15 mM) of ammonium ion increased the production of nanaomycin, while larger... 

Seinmelhack, M.F., Bozell, (.(., Sato, T, WuUF, W Spiess, E. and Zask, A. (1982) Synthesis of nanaomycin a and deoxyfrenolicin by alkyne cycloaddition to chromiumAmerican Chemical Society, 104, 5850-5853. 

SemmeUiack ME, BozeU JJ, Sato T, Wulf W, Spies E, Zask A. Synthesis of nanaomycine A and deoxyfrenolicin by alkyne cycloaddition to chromium-carbene complexes. J. Am. Chem. Soc. 1982 104 5850-5852. 

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