发明授权
US5981770A Method for the preparation of (+)-calanolide A and analogues thereof
失效
制备（+） - 蒎烯内酯A及其类似物的方法
- 专利标题： Method for the preparation of (+)-calanolide A and analogues thereof
- 专利标题（中）： 制备（+） - 蒎烯内酯A及其类似物的方法
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申请号： US924840申请日： 1997-09-05
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公开(公告)号： US5981770A公开(公告)日： 1999-11-09
- 发明人: Michael T. Flavin , Ze-Qi Xu , Albert Khilevich , David Zembower , John D. Rizzo , Shuyuan Liao , Aye Mar , Lin Lin , Vilayphone Vilaychack , Darko Brankovic , Sergey Dzekhster , Jinjun Liu
- 申请人： Michael T. Flavin , Ze-Qi Xu , Albert Khilevich , David Zembower , John D. Rizzo , Shuyuan Liao , Aye Mar , Lin Lin , Vilayphone Vilaychack , Darko Brankovic , Sergey Dzekhster , Jinjun Liu
- 申请人地址： IL Lemont
- 专利权人： Sarawak MediChem Pharmaceuticals, Inc.
- 当前专利权人： Sarawak MediChem Pharmaceuticals, Inc.
- 当前专利权人地址： IL Lemont
- 优先权： WOXPCT/US95/09804 19950802
- 主分类号： A61K45/06
- IPC分类号： A61K45/06 ; C07D311/16 ; C07D493/04 ; C07D493/14 ; C07D493/00
摘要：
A method of preparing (+)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. According to the disclosed method, chromene 4 intermediate was subjected to a chlorotitanium-mediated aldol reaction with acetaldehyde to selectively produce (.+-.)-8a. Separation and enzyme-mediated resolution of (.+-.)-8a produced (+)-8a. Cyclization of (+)-8a under neutral Mitsunobu conditions followed by Luche reduction of (+)-7 produced (+)-calanolide A in high yield and enantiomeric purity. The method of the invention has been extended to produce potent antiviral calanolide A analogues.
公开/授权文献
- US4720956A Plate profile 公开/授权日：1988-01-26
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