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An easy preparation of (−) and (+)-β-piperonyl-γ-butyrolactones, key-intermediates for the synthesis of optically active lignans

✍ Scribed by Eric Brown; Alain Daugan

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
127 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

Methyl ~-piperonylhemisuccinate was resolved into both its (R)-(t) and (S)-(-Iantipodes by (-) and (+)-ephedrine, respectively. Calcium borohydride reduction of the (R)-(t) and (S)-(-)-hemiesters afforded the crystalline, o.ptically pure, (R)-(t) and (S)-t-k B-piperonyl-y-butyrolactones, respectively, and in high yields. The latter were converted into (-) and (t)-isodeoxypodophyllotoxin, respectively.

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