Synthesis of 4,4-Dimethoxybut-1-Yne

doi:10.1002/0471264229.OS092.02

Paper

Synthesis of 4,4-Dimethoxybut-1-Yne

Published 2015 · James Z. Deng, Yu-Pu Wang, R. Danheiser

Organic Syntheses

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Abstract

4,4-Dimethoxybut-1-yne is a valuable difunctional synthetic building block which incorporates a masked aldehyde carbonyl group and terminal alkyne within a four-carbon chain. To date this versatile synthon has found application as a key intermediate in the synthesis of heterocyclic compounds, functionalized alkenes, and several classes of biomolecules including carbohydrates, polyketides, and lipids. This article reports an efficient route to the formation of 4,4-dimethoxybut-1-yne, which was employed as a key building block in the tandem benzannulation/cyclization strategy for the synthesis of highly substituted indoles developed.

Study Snapshot

This study presents an efficient route to the formation of 4,4-dimethoxybut-1-yne, a valuable difunctional synthetic building block, which can be used as a key intermediate in the synthesis of highly substituted indoles.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of 4,4-Dimethoxybut-1-Yne

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References

Benzannulation via the reaction of ynamides and vinylketenes. application to the synthesis of highly substituted indoles.

The two-stage tandem strategy enables the synthesis of highly substituted indoles by combining benzannulation with various cyclization and annulation processes.

Copper‐Catalyzed Preparation of γ‐Alkylidenebutenolides and Isocoumarins under Mild Palladium‐Free Conditions

Copper(I)-catalyzed cross-coupling and heterocyclization reaction efficiently produces 5-ylidenebutenolides and 3-substituted isocoumarins under mild, palladium-free conditions, with excellent regio- and stereoselectivity.

Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids.

This study demonstrates efficient and selective dichlorination of allylic alcohol derivatives to access key stereochemical arrays in the chlorosulfolipid class of natural products.

A unified synthetic approach to polyketides having both skeletal and stereochemical diversity.

This efficient synthetic approach efficiently creates polyketides with both skeletal and stereochemical diversity, enabling a 74-membered library of six different skeletal classes in one to five steps from propargylic alcohol precursors.

Highly Stereoselective Palladium Catalysed Cross-Coupling Approaches to the Total Synthesis of Phthoxazolin A

The study presents a highly stereoselective palladium-catalyzed cross-coupling method for the total synthesis of racemic Phthoxazolin A4, using vinylboronate pinacol ester 1.

Asymmetric synthesis of carbohydrates: Synthesis of 2-deoxy-D- and 2-deoxy-L-xylofuranosides from a simple achiral precursor

Asymmetric dihydroxylation of alkenes can produce 2-deoxy-D- and 2-deoxy-L-xylofuranosides from acetylenic alcohol, with a 50% overall yield.

Effect of coordinating ligands on the Pauson-Khand cycloaddition: trapping of an intermediate

The Pauson-Khand cycloaddition reaction can be further enhanced by trapping an intermediate in the 1,6-enyne position, potentially leading to more efficient synthetic processes.

Substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents: a route to allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals

Substituting dialkoxymethylacetates' acetoxy groups with organometallic reagents can produce functional acetals like allyl-, propargyl-, homoallyl-, homopropargyl-, and -stannylacetals.

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