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Updated: Jul 28, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Carbon hydroxylation of alkyltetrahydropyranols: a paradigm for spiroacetal biosynthesis in Bactrocera sp
J E Stok1, C S Lang, B D Schwartz
1Department of Chemistry, University of Queensland, Brisbane, 4072 Australia.
Abstract:
[figure: see text] 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.
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