A convenient preparation of (S)-(−)-4-hydroxy-2-methylcyclopent-2-en-1-one and its application as a chiral synthetic equivalent of 2-methylcyclopent-2-en-1-one in the terpenoid synthesis

A method for the preparation of (S)-4-hydroxy-2-methylcyclopent-2-en-1-one from 1-(2-furyl)ethanol using modified Piancatelli rearrangement and enzymatic kinetic resolution of the racemate was developed. An application of O-protected derivatives of 4-hydroxy-2-methylcyclopent-2-en-1-one to terpenoid...

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Veröffentlicht in:Tetrahedron 2014-08, Vol.70 (34), p.5073-5081
Hauptverfasser: Michalak, Karol, Wicha, Jerzy
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creator Michalak, Karol
Wicha, Jerzy
description A method for the preparation of (S)-4-hydroxy-2-methylcyclopent-2-en-1-one from 1-(2-furyl)ethanol using modified Piancatelli rearrangement and enzymatic kinetic resolution of the racemate was developed. An application of O-protected derivatives of 4-hydroxy-2-methylcyclopent-2-en-1-one to terpenoid synthesis through tandem conjugate addition of allyl-metal reagents, enolate trapping, and consecutive Mukaiyama–Michael addition was studied. An optically active azulene derivative useful for terpenoid synthesis was efficiently synthesized. [Display omitted]
doi_str_mv 10.1016/j.tet.2014.06.006
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subjects Azulene
Conjugate addition
Conjugates
Derivatives
Equivalence
Kinetic resolution
Optical activity
Piancatelli rearrangement
Synthesis (chemistry)
Tantalum pentachloride
Tetraallylstannane
Tetrahedrons
Total synthesis
Trapping
title A convenient preparation of (S)-(−)-4-hydroxy-2-methylcyclopent-2-en-1-one and its application as a chiral synthetic equivalent of 2-methylcyclopent-2-en-1-one in the terpenoid synthesis
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