Diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols. Absolute stereochemistry of (E,E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol and of (E,E)-8-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)methanol present in Bactrocera cucumis

doi:10.1021/JO00038A027

Paper

Diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols. Absolute stereochemistry of (E,E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol and of (E,E)-8-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)methanol present in Bactrocera cucumis

Published Jun 1, 1992 · M. Perkins, M. F. Jacobs, W. Kitching

Journal of Organic Chemistry

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Abstract

Routes to the four regioisomeric 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols have been developed, and in the racemic series, mercury(II)-mediated reactions of appropriate dienone, hydroxy enone, dienedione, and hydroxy dienone systems have been exploited. Most of the epimeric pairs of alcohols (i.e. axial or equatorial) in the EE, EE, or ZE spiroacetal ring systems have been characterized by detailed H, C, and correlated NMR spectroscopy and mass spectrometry. Key enantiomers of these alcohols have been obtained by elaborating chiral starting materials such as D-mannitol, L-arabinose, poly(hydroxybutyrate), and in the case of the 5-hydroxy derivative, mandelonitrile lyase mediated formation of a key chiral cyanohydrin was employed. Most of the alcohols, as their trifluoroacetates, are resolved (into enantiomers) on a Lipodex A GC column, thus facilitating their identification from natural sources. In this way, the absolute configurations of a number of 2,8-dimethyl-l,7-dioxaspiro[5.5]undecanols present in the rectal gland secretion of Bactrocera cucumis (cucumber fly) have been determined.

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This study developed diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols from Bactrocera cucumis (cucumber fly) rectal gland secretion, enabling

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols. Absolute stereochemistry of (E,E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol and of (E,E)-8-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)methanol present in Bactrocera cucumis

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References

Citations

Synthesis, Reactions and Application of 2,2-Dimethyl-4-oxymethyl-1,3-dioxolane (A Review)

2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane is essential for drug production and its synthesis and use in organic synthesis are reviewed in this review.

Review of cucumber fruit fly, Bactrocera cucumis (French) (Diptera: Tephritidae: Dacinae): Part 2, biology, ecology and control in Australia

Bactrocera cucumis fruit fly is a lesser known Australian fruit fly with large eggs, a high reproduction rate, and can be managed using chemosterilants, sterile insect techniques, and chemical sprays.

Stereoselective total synthesis of dinemasone A by double intramolecular hetero-Michael addition (DIHMA).

Dinemasone A can be synthesized with high stereoselectivity using a double intramolecular hetero-Michael addition strategy, enabling its potential use in pharmaceuticals and bioactive compounds.

Biosynthesis of insect spiroacetals.

Insect spiroacetals, found in beetle, wasp, and dipteran secretions, may serve as sex pheromones, and understanding their biosynthesis may help understand their role in insect life.

Furanyl spiroketals as stereochemical relays in the synthesis of 1,9-anti diols: synthesis of insect pheromones

Furanyl spiroketals can effectively synthesize insect pheromones with high diastereoselectivity, as demonstrated by the synthesis of the swede midge pheromone.

Identification of Male-Specific Chiral Compound from the Sugarcane Weevil Sphenophorus levis

The male-specific compound 2-methyl-4-octanol in sugarcane weevils may elicit aggregation behavior among adults, similar to other curculionid species.