The 'Reverse Polarity' Approach to Ravidomycin. Aryl C‐Aminoglycosides from a Lithiated Aminoglycal

Autor:	Kathlyn A. Parker, Dai‐Shi Su
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Glycal Stereochemistry Aryl Organic Chemistry Aromatization Biochemistry Adduct Quinone Umpolung chemistry.chemical_compound Hydroboration Stereospecificity chemistry
Zdroj:	Journal of Carbohydrate Chemistry. 24:187-197
ISSN:	1532-2327 0732-8303
DOI:	10.1081/car-200059957
Popis:	A three‐step sequence affects the regio‐ and stereospecific elaboration of an aryl C‐aminoglycoside from a simple aminoglycal and a quinone. Direct lithiation of the glycal followed by addition of the quinone, reduction of the quinol adduct, and hydroboration gives a product with a trans‐trans stereochemical relationship between the substituents at C1′, C2′, and C3′, appropriate for compounds in the ravidomycin series.
Databáze:	OpenAIRE
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