摘要 |
<p>PURPOSE:To obtain the subject optically active compounds of high purity useful as an intermediate of an antibiotics anisomycin and derivatives thereof free from generation of racemization by dehydration of a hydroxypyrrolidine compound. CONSTITUTION:A compound of formula I (Ar is substituted or non-substituted aryl; Z is protecting group for amino group; * is optically active carbon) is dehydrated to obtain an optically active 3,4-dehydropyrrolidine compound of formula II. The N-protecting group is furthermore removed as necessary to obtain an N-free form of the compound of formula II. As the dehydration method therefor, the compound of formula I is reacted initially with carbon disulfide and then with a compound R<1>X<2> (R<1> is alkyl or aralkyl; X<2> is halogen or sulfonyloxy) to synthesize a compound of formula III and the resultant compound is then subjected to an elimination reaction. Or as another method, the compound of formula I is treated with an acid. By the above mentioned methods, various homologous compounds belonging to the compounds of formula II can be obtained.</p> |