Synthesis of quinone pyrano-gamma-lactone antibiotics and antifu

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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2603478, C07D49304

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active

042370574

ABSTRACT:
An efficient synthesis of quinone pyrano-gamma-lactone antibiotics such as kalafungin and the new compound 9-deoxykalafungin in four basic steps from readily available starting materials. The key step in which all of the carbon atoms present in the target molecule are assembled is the addition of an alkoxy furan to a two position functionally substituted 1,4 naphthoquinone. This is followed by alkylating to provide protecting groups, hydride reduction, removal of the protecting groups, internal cyclization and by oxidative dealkylation to provide practical overall yields of the desired antibiotics.

REFERENCES:
Omura et al. Jour. Chem. Soc. Chem. Comm. pp. 320-321, 1976.
Bergy The Journ. of Antibiotics 21, Jul. 1969, pp. 454-457.

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