Synthesis of optically active lactones from L-aspartic acid and

Details Synthesis of optically active lactones from L-aspartic acid and Synthesis of optically active lactones from L-aspartic acid and

1991-06-03

1994-06-21

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

546283, 548517, 549295, 549322, 549323, C07D23920, C07D30733

Patent

active

053229428

ABSTRACT:
Optically active lactones are described, such as an intermediate lactone having the formula ##STR1## where R and R.sup.2 are each independently alkyl with 1 to 6 carbon atoms, cycloalkyl with 6 to 10 carbon atoms, aryl with 6 to 10 carbon atoms, or arylalkyl with 7 to 19 carbon atoms, R.sup.4 is H or C.sub.1-6 alkyl, and Ar is a homo- or heteroaromatic ring with 5 or 6 ring atoms being optionally substituted by C.sub.1-6 alkyl or alkoxy groups, halogen atoms, cyano or nitro groups. Such optically active, intermediate lactones are prepared from L-aspartic acid, and can be readily converted to (+)-pilocarpine and its analogues by hydrolysis, reduction, and hydrogenation, such as to an optically active lactone having the formula ##STR2## which is (+)-pilocarpine when R is ethyl, R.sup.4 is H, and Ar is 1-methylimidazol-5-yl.

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