Synthesis of Optically Active 5-(tert-Butyldimethylsiloxy)-2-cyclohexenone and Its 6-Substituted Derivatives as Useful Chiral Building Blocks for the Synthesis of Cyclohexane Rings. Syntheses of Carvone, Penienone, and Penihydrone

doi:10.1021/JA9843122

Paper

Synthesis of Optically Active 5-(tert-Butyldimethylsiloxy)-2-cyclohexenone and Its 6-Substituted Derivatives as Useful Chiral Building Blocks for the Synthesis of Cyclohexane Rings. Syntheses of Carvone, Penienone, and Penihydrone

Published Apr 6, 1999 · G. Hareau, Masakazu Koiwa, S. Hikichi

Journal of the American Chemical Society

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58

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Abstract

Optically active 5-(tert-butyldimethylsiloxy)-2-cyclohexenone (1) and its 6-substituted derivatives 2a,b were synthesized from the readily available optically active ethyl 3-(tert-butyldimethylsiloxy)-5-hexenoate (4), where the Ti(II)-mediated intramolecular nucleophilic acyl substitution reaction and the FeCl3-mediated ring expansion reaction of a 1-hydroxybicyclo[3.1.0]hexane are the key reactions. The enone 1 reacted with higher-order cyanocuprates with excellent diastereoselectivity to afford the trans-addition products, trans-13, in excellent yields. The reaction of 1 with lower-order cyanocuprates proceeded with moderate to excellent syn-selectivity to afford cis-13. Treatment of trans- and cis-13 with DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or catalyst p-TSA (p-toluenesulfonic acid) resulted in a β-elimination reaction to furnish the corresponding optically active 5-substituted-2-cyclohexenones 14. The 1,4-addition reaction of 2a and 2b with organocyanocuprates followed by treatment of the resulti...

Study Snapshot

Optically active 5-(tert-butyldimethylsiloxy)-2-cyclohexenone and its 6-substituted derivatives are useful chiral building blocks for the synthesis of cyclohexane rings, including carvone, penienone, and pen

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 Optically Active 5-(tert-Butyldimethylsiloxy)-2-cyclohexenone and Its 6-Substituted Derivatives as Useful Chiral Building Blocks for the Synthesis of Cyclohexane Rings. Syntheses of Carvone, Penienone, and Penihydrone

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References

Citations

Synthetic Efforts toward Lannotinidine G Based on an Aziridinium-Mediated Ring Contraction and Dienyne Metathesis.

Our synthetic strategy successfully achieved the synthesis of Lannotinidine G using aziridinium-mediated ring contraction and dienyne metathesis.

Rhodium-Catalyzed Asymmetric Addition to 4- or 5-Carbonyl-cycloenones through Dynamic Kinetic Resolution: Enantioselective Synthesis of (-)-Cannabidiol.

Rhodium-catalyzed asymmetric addition to 4- or 5-carbonyl-cycloenones leads to enantioselective synthesis of (-)-cannabidiol, with potential applications in key intermediates for (-)-cannabidiol.

Synthesizing cyclohex-2-enone derivatives and exploring their bioactivities for drug discovery

Cyclohex-2-enone derivatives show potential for drug discovery due to their wide range of pharmacological activities, including anti-cancer, anti-bacterial, anti-inflammatory, and anti-neuropathic properties.

Enantioselective Organocatalytic Conjugate Addition in a Tandem Synthesis of δ-Substituted Cyclohexenones and Four-Step Total Synthesis of Penienone.

This study demonstrates a novel organocatalytic conjugate addition method for synthesizing chiral -substituted cyclohexenones and their use in a four-step total synthesis of penienone with high yields and enantioselectivity

Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complex.

Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complexes leads to the conversion of various substrates into multi-substituted cyclohexenones in good yields.