Efficient and selective reduction protocols of the 2,2-dimethyl-1,3-benzodioxan-4-one functional group to readily provide both substituted salicylaldehydes and 2-hydroxybenzyl alcohols.

doi:10.1021/JO0601664

Paper

Efficient and selective reduction protocols of the 2,2-dimethyl-1,3-benzodioxan-4-one functional group to readily provide both substituted salicylaldehydes and 2-hydroxybenzyl alcohols.

Published Apr 6, 2006 · Naval Bajwa, M. Jennings

The Journal of organic chemistry

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Abstract

Two complementary procedures have been developed that selectively allow for the synthesis of either substituted salicylaldehydes or the corresponding 2-hydroxylbenzyl alcohols upon treatment of the 2,2-dimethyl-1,3-benzodioxan-4-one functional group with DIBAL-H or LAH, respectively.

Study Snapshot

Selective reduction protocols of the 2,2-dimethyl-1,3-benzodioxan-4-one functional group enable the synthesis of both substituted salicylaldehydes and 2-hydroxybenzyl alcohols.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Efficient and selective reduction protocols of the 2,2-dimethyl-1,3-benzodioxan-4-one functional group to readily provide both substituted salicylaldehydes and 2-hydroxybenzyl alcohols.

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References

Citations

Synthesis of functionalized benzo[1,3]dioxin-4-ones from salicylic acid and acetylenic esters and their direct amidation

Direct synthesis of functionalized benzo[1,3]dioxin-4-ones from salicylic acid and acetylenic esters leads to salicylamides in moderate to good yields.

Synthesis of (12R,13S)-pyriculariol and (12R,13S)-dihydropyriculariol revealed that the rice blast fungus, Pyricularia oryzae, produces these phytotoxins as racemates.

The rice blast fungus, Pyricularia oryzae, produces racemic phytotoxins with both salicylaldehyde core and side chain essential for phytotoxic activity, and their synthesis requires both optical and aerated jar fermenter methods.

Revisiting the Addition of in-situ Nucleophiles to Allenic Ketones: An Entry Towards Synthesis of Benzodioxins

This study presents a green, environmentally friendly method for regioselective addition of negative nucleophiles to allenic ketones, leading to the synthesis of benzodioxin skeletons.

Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactions.

Secondary amine-catalyzed dual Michael cascade reactions efficiently synthesize valuable benzodioxins with a 2-site quaternary carbon structure, offering a new reaction route for ynone species.

Bioinspired Total Synthesis and Stereochemical Revision of the Fungal Metabolite Pestalospirane B.

The bioinspired tandem dimerization-spiroketalization reaction successfully synthesized both enantiomers of pestalospirane B, enabling a revision of its absolute stereochemistry from 3S, 3'S, 12R, 12'R to 3R, 3'R, 12S, 12