Carbon Hydroxylation of Alkyltetrahydropyranols:  A Paradigm for Spiroacetal Biosynthesis in Bactrocera sp

In a number of Bactrocera species the penultimate step in the biosynthesis of spiroacetals is shown to be the hydroxylation of an alkyltetrahydropyranol followed by cyclization. The monooxygenases that catalyze this side chain hydroxylation show a strong preference for oxidation four carbons from th...

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Bibliographic Details
Published in:Organic letters 2001-02, Vol.3 (3), p.397-400
Main Authors: Stok, Jeanette E, Lang, Cheng-Shan, Schwartz, Brett D, Fletcher, Mary T, Kitching, William, De Voss, James J
Format: Article
Language:English
Subjects:
Acetals - metabolism
Animals
Diptera - metabolism
Female
Hydroxylation
Male
Mixed Function Oxygenases - metabolism
Oxidation-Reduction
Pyrans - metabolism
Spiro Compounds - metabolism
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Summary:In a number of Bactrocera species the penultimate step in the biosynthesis of spiroacetals is shown to be the hydroxylation of an alkyltetrahydropyranol followed by cyclization. The monooxygenases that catalyze this side chain hydroxylation show a strong preference for oxidation four carbons from the hemiketal center, to produce the spiroacetal. The hydroxy spiroacetals observed in Bactrocera appear to derive from direct oxidation of the parent spiroacetals and not from alternate precursors.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0069047