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Studies toward the total synthesis of pluraflavin A.

ABSTRACT: A synthetic strategy towards the potent cytostatic agent pluraflavin A has been developed. Formation of the enantioenriched anthrapyran core bearing a halogen atom enabled the introduction of the ??C-aryl glycoside by Stille cross-coupling and subsequent hydrogenation of the aryl glycal. Chemo- and stereoselective O-glycosylations of ??oliose and ??3-epi vancosamine residues afforded a fully glycosylated aromatic core. Attempts to install the dimethylamino group of the C-disaccharide suggest that introduction of an azide group by displacement and subsequent reduction may pave the way to the total synthesis of pluraflavin A.

SUBMITTER: Hartung J

PROVIDER: S-EPMC4795151 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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Studies toward the total synthesis of pluraflavin A.

Hartung John J J D Wright Benjamin B Danishefsky Samuel J SJ

Chemistry (Weinheim an der Bergstrasse, Germany) 20140612 28

A synthetic strategy towards the potent cytostatic agent pluraflavin A has been developed. Formation of the enantioenriched anthrapyran core bearing a halogen atom enabled the introduction of the α C-aryl glycoside by Stille cross-coupling and subsequent hydrogenation of the aryl glycal. Chemo- and stereoselective O-glycosylations of α oliose and β 3-epi vancosamine residues afforded a fully glycosylated aromatic core. Attempts to install the dimethylamino group of the C-disaccharide suggest tha ...[more]

PMID: 24919792

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