Practical Synthesis of Chiral Emopamil Left Hand as a Bioactive Motif
The Journal of Organic Chemistry2002Vol. 67(17), pp. 6228–6231
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Teiji Kimura, Noboru Yamamoto, Yuichi Suzuki, Koki Kawano, Yoshihiko Norimine, Koichi Ito, Satoshi Nagato, Yoichi Iimura, Masahiro Yonaga
Abstract
An asymmetric synthesis of (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile (emopamil left hand, 2) has been completed by use of the MAD (methyl aluminum bis(4-methyl-2,6-di-tert-butylphenoxide)-induced rearrangement of a chiral epoxyalcohol as the key reaction. The stereochemistry of the chiral quaternary center was confirmed by transformation of 2 to (S)-noremopamil. This method requires minimal purification procedures and affords high chemical and optical yields. Acid-catalyzed isomerization of an allylaldehyde and retro-aldol type racemization at the quaternary carbon of a nitrile-alcohol were encountered.
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