Chemoenzymatic Synthesis of Carbasugars (+)-Pericosines A−C from Diverse Aromatic cis-Dihydrodiol Precursors

cis-Dihydrocatechols, derived from biological cis-dihydroxylation of methyl benzoate, iodobenzene and benzonitrile, using the microorganism Pseudomonas putida UV4, were converted into pericosines A, C, and B, respectively. This approach constitutes the shortest syntheses, to date, of these important...

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Bibliographic Details
Published in:Organic letters 2010-05, Vol.12 (10), p.2206-2209
Main Authors: Boyd, Derek R, Sharma, Narain D, Acaru, Carmen A, Malone, John F, O’Dowd, Colin R, Allen, Christopher C. R, Stevenson, Paul J
Format: Article
Language:English
Subjects:
Molecular Conformation
Naphthalenes - chemistry
Shikimic Acid - analogs & derivatives
Shikimic Acid - chemical synthesis
Shikimic Acid - chemistry
Stereoisomerism
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Summary:cis-Dihydrocatechols, derived from biological cis-dihydroxylation of methyl benzoate, iodobenzene and benzonitrile, using the microorganism Pseudomonas putida UV4, were converted into pericosines A, C, and B, respectively. This approach constitutes the shortest syntheses, to date, of these important natural products with densely packed functionalities.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100525r