Asymmetric synthesis of the 2,2,3-trisubstituted cyclopentanone, D-ring fragment of 9,11-secosterols

Kõllo, Marek; Aav, Riina; Tamp, Sven; Jarvet, Jüri; Lopp, Margus

doi:10.1016/j.tet.2014.07.079

Cited by 4 publications

(2 citation statements)

References 28 publications

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“…Starting material 2 was recovered in 36% yield (72 mg). The spectral data matched those found in literature [3][4][5][6][7][8][9]27,35,36].…”

Section: Asymmetric Oxidation -Standard Proceduressupporting

confidence: 87%

“…Since the discovery of highly bioactive 9,11-secosterols [1][2][3], our research group has been involved in the elaboration of the chemical access to that family of compounds [4][5][6][7][8]. In eighties of the last century Posner et al demonstrated that substituted cyclopentenone sulfoxides can be used as Michael acceptors for 1-tetralone enolates [9][10][11] .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2-(S)-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one, a D-ring precursor of 9,11-secosterols

Kõllo¹,

Rõuk²,

Lopp³

2022

PEAS

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The asymmetric oxidation of a key intermediate for 9,11-secosterol synthesis, 2-[(4-methylphenyl)thio]-2-cyclopenten-1one 2 with a Ti(iPrO) 4 /(+)-DET/TBHP complex was studied. The kinetic resolution of racemic 2-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one 1 by oxidation with the same Ti-complex was also carried out. In both cases enantioenriched 2-(S)-[(4methylphenyl)sulfinyl]-2-cyclopenten-1-one 1 was obtained in satisfactory yields and sufficient enantiomeric purity for further enantioenrichment by recrystallization. The obtained results afford simple access to the D-ring precursor of 9,11-secosterols.

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“…Starting material 2 was recovered in 36% yield (72 mg). The spectral data matched those found in literature [3][4][5][6][7][8][9]27,35,36].…”

Section: Asymmetric Oxidation -Standard Proceduressupporting

confidence: 87%