An efficient stereocontrolled synthesis of the potent C17,20- lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1- propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale.
All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry