The derivation of a novel mitomycin skeleton: 3.ALPHA.-Alkoxymitomycin

Autor:	Kunikatsu Shirahata, Masaji Kasai, Motomichi Kono
Rok vydání:	1991
Předmět:	Pharmacology Molecular Structure Hydroquinone Stereochemistry Mitomycin D Mitomycin B Alpha (ethology) Iminium Mass Spectrometry Mitomycins chemistry.chemical_compound chemistry Porfiromycin Drug Discovery Alkoxide Oxidation-Reduction Alkoxylation
Zdroj:	The Journal of Antibiotics. 44:301-308
ISSN:	1881-1469 0021-8820
DOI:	10.7164/antibiotics.44.301
Popis:	The first example of C-3 alkoxylation in mitomycins has been achieved. 3 alpha-iso-Propoxy-10-O-decarbamoylmitomycin D (4) and 3 alpha-iso-propoxymitomycin D (5) were derived from mitomycin D (3) under decarbamoylation conditions with iso-propoxide. Under similar conditions 3 alpha-iso-propoxy-10-O-decarbamoylporfiromycin (8) and 3 alpha-methoxy-10-O-decarbamoylmitomycin B (11) were also derived from porfiromycin (6) and mitomycin B (9), respectively. The mechanism of generation of these novel analogs was based on the premise that the key intermediate of hydroquinone iminium salt (14) was led through the iminium salt (13), followed by alkoxide addition and oxidation.
Databáze:	OpenAIRE
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