Highly Stereoselective Alkynylation with Steroidal Alkyne: Efficient Pathway to 24(S) or 24(R)-Hydroxylcholesterol

Biao      Jiang; Zi-li      Chen; Hao      Huang

doi:10.2174/1570178054038911

Abstract

24(S)- or 24(R)-Hydroxyl cholesterol was prepared in high stereoselectivity (up to 99% de), utilizing asymmetric alkynylation of isobutyraldehyde with steroidal alkyne catalyzed by Zn(OTf)2 respectively in the presence of (1S, 2S)-3-(t-butyldimethylsilyloxyl)-2-N, N-dimethylamino-1-(p-nitrophenyl)- propane-1-ol or its (1R, 2R)-enantiomer.

Keywords: asymmetric alkynylation, hydroxylcholesterol, hyodeoxycholic acid

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Letters in Organic Chemistry

Title: Highly Stereoselective Alkynylation with Steroidal Alkyne: Efficient Pathway to 24(S) or 24(R)-Hydroxylcholesterol

Volume: 2 Issue: 4

Author(s): Biao Jiang, Zi-li Chen and Hao Huang

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Keywords: asymmetric alkynylation, hydroxylcholesterol, hyodeoxycholic acid

Abstract: 24(S)- or 24(R)-Hydroxyl cholesterol was prepared in high stereoselectivity (up to 99% de), utilizing asymmetric alkynylation of isobutyraldehyde with steroidal alkyne catalyzed by Zn(OTf)2 respectively in the presence of (1S, 2S)-3-(t-butyldimethylsilyloxyl)-2-N, N-dimethylamino-1-(p-nitrophenyl)- propane-1-ol or its (1R, 2R)-enantiomer.

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Jiang Biao, Chen Zi-li and Huang Hao, Highly Stereoselective Alkynylation with Steroidal Alkyne: Efficient Pathway to 24(S) or 24(R)-Hydroxylcholesterol, Letters in Organic Chemistry 2005; 2 (4) . https://dx.doi.org/10.2174/1570178054038911