Asymmetric One-Pot Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol: A Key Component of Current HIV Protease Inhibitors.

doi:10.1021/acs.joc.6b02588

Paper

Asymmetric One-Pot Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol: A Key Component of Current HIV Protease Inhibitors.

Published Jan 4, 2017 · Adrian Sevenich, Gong-Qing Liu, A. Arduengo

The Journal of organic chemistry

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Abstract

A concise and efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol, a key building block for several clinical and experimental HIV protease inhibitors including the highly important drug darunavir, was achieved via a one-pot procedure using furan and Cbz-protected glycol aldehyde as starting materials. A [2+2]-photocycloaddition between both reactants which can be prepared from wood-based starting materials according to the principles of xylochemistry, followed by hydrogenation and lipase-catalyzed kinetic resolution afforded the target compound in high yield and up to 99% ee.

Study Snapshot

This one-pot method efficiently synthesizes (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol, a key component of HIV protease inhibitors, with high yield and up to 99% ee.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Asymmetric One-Pot Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol: A Key Component of Current HIV Protease Inhibitors.

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References

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This study demonstrates that biocatalysis in microaqueous solvent systems can produce all four stereoisomers of 1,2-diol at high product concentrations, with potential applications in pharmaceuticals.

Research and Development of an Efficient Synthesis of a Key Building Block for Anti-AIDS Drugs by Diphenylprolinol-Catalyzed Enantio- and Diastereoselective Direct Cross Aldol Reaction

This study developed an efficient method for synthesizing 1-([(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl-oxy)pyrrolidine-2,5-dione (1), a key

A Bioinspired Cyclization Sequence Enables the Asymmetric Total Synthesis of Dictyoxetane.

This study successfully synthesized (+)-dictyoxetane using a bioinspired cyclization sequence, enabling the first dyotropic rearrangement of an epoxide-oxetane substrate.

A Concise One‐Pot Organo‐ and Biocatalyzed Preparation of Enantiopure Hexahydrofuro[2,3‐b]furan‐3‐ol: An Approach to the Synthesis of HIV Protease Inhibitors

This one-pot method efficiently synthesizes enantiopure hexahydrofuro[2,3-b]furan-3-ol, a crucial component of HIV protease inhibitors, with potential applications in treating multi-drug-resistant HIV.

Recent Progress in the Development of HIV-1 Protease Inhibitors for the Treatment of HIV/AIDS.

Current drug design and medicinal chemistry efforts are focused on developing next-generation HIV-1 protease inhibitors to enhance the treatment of HIV/AIDS.

Citations

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