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Convergent de novo synthesis of vineomycinone B2 methyl ester.

ABSTRACT: An efficient de novo synthesis of vineomycinone B2 methyl ester has been achieved. The longest linear route required only 14 steps from achiral commercially available starting materials (4.0% overall yield). The key transformations included the de novo asymmetric synthesis of two key fragments, which were joined by a convergent late stage Suzuki's glycosylation for the construction of the aryl ?-C-glycoside. A subsequent BBr3 one-pot debenzylation, demethylation and air oxidation provided vineomycinone B2 methyl ester.

SUBMITTER: Chen Q

PROVIDER: S-EPMC3871180 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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Convergent de novo synthesis of vineomycinone B2 methyl ester.

Chen Qian Q Zhong Yashan Y O'Doherty George A GA

Chemical communications (Cambridge, England) 20130801 60

An efficient de novo synthesis of vineomycinone B2 methyl ester has been achieved. The longest linear route required only 14 steps from achiral commercially available starting materials (4.0% overall yield). The key transformations included the de novo asymmetric synthesis of two key fragments, which were joined by a convergent late stage Suzuki's glycosylation for the construction of the aryl β-C-glycoside. A subsequent BBr3 one-pot debenzylation, demethylation and air oxidation provided vineom ...[more]

PMID: 23778961

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