An Expedient Synthesis of 6-Fluoroursodeoxycholic Acid
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- 作者：Kurt Kö ; nigsberger ; Guang-Pei Chen ; James Vivelo ; George Lee ; John Fitt ; Joseph McKenna ; Todd Jenson ; Kapa Prasad ; and Oljan Repi
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- 刊名：Organic Process Research & Development
- 出版年：2002
- 出版时间：September 2002
- 年：2002
- 卷：6
- 期：5
- 页码：665 - 669
- 全文大小：85K
- 年卷期：v.6,no.5(September 2002)
- ISSN：1520-586X
文摘
Optimization of the synthesis of 6
-fluoroursodeoxycholic acid1 is described starting from the commercially available 2. Thepenultimate intermediate 16 was made in eight synthetic stepsbut in only four operations in an overall yield of 57%. Thehighlights are flourination of hydroxyketo acid 11 using Selectfluor through the intermediacy of silyl enol ether 12,conversion of 13 to 14 via equilibration of fluoroketone,esterification, and acylation. The drug substance 1 was preparedfrom mesylate 16 using potassium superoxide followed by a mildreductive workup using methoxydiethylborane.
-fluoroursodeoxycholic acid1 is described starting from the commercially available 2. Thepenultimate intermediate 16 was made in eight synthetic stepsbut in only four operations in an overall yield of 57%. Thehighlights are flourination of hydroxyketo acid 11 using Selectfluor through the intermediacy of silyl enol ether 12,conversion of 13 to 14 via equilibration of fluoroketone,esterification, and acylation. The drug substance 1 was preparedfrom mesylate 16 using potassium superoxide followed by a mildreductive workup using methoxydiethylborane.