An efficient chiral moderator prepared from inexpensive (+)3-carene: Synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963

被引:183
作者
Kauffman, GS [1 ]
Harris, GD [1 ]
Dorow, RL [1 ]
Stone, BRP [1 ]
Parsons, RL [1 ]
Pesti, JA [1 ]
Magnus, NA [1 ]
Fortunak, JM [1 ]
Confalone, PN [1 ]
Nugent, WA [1 ]
机构
[1] Dupont Merck Pharmaceut Co, Chem Proc R&D, Chambers Works, Deepwater, NJ 08023 USA
关键词
D O I
10.1021/ol006321x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The beta-amino alcohol 4 beta-morpholinocaran-3 alpha-ol is prepared by addition of morpholine to alpha-3,4-epoxycarane utilizing anhydrous magnesium bromide as Lewis acid promoter. The enantiopure amino alcohol is uniquely effective as a chiral moderator for the addition of lithium cyclopropylacetylide to an unprotected N-acylketimine. This reaction provides an efficient route to the second generation NNRTI drug candidate DPC 963.
引用
收藏
页码:3119 / 3121
页数:3
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