• 약학회지
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• 제39권4호
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• pp.461-464
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• 1995

7, 8-Dioxp-A-norerythrinan-6-carboxylates (1-2) were synthesized by acid catalyzed cyclization of 2, 3-dioxo-1-phenethyl-octahydrocyclopenta[b]pyrrole-3a-carboxylates (3-6). The preparative condition and characteristic of rigid A-norerythrinan skeleton (E) were discussed with brief interpretation.

• 약학회지
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• 제38권1호
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• pp.86-90
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• 1994

7,8-Dioxo-A-norerythrinan (A) was synthesized from acid catalyzed cyclization of 6a-hydroxv-1-(2-phenylethyl)-octahydrocyclo-penta[b] pyrrole-3a-carboxylic acid ethyl ester (B) with concomitant deethoxycarbonylation. The intermediate (B) was a hydroxylated compound of N-acyliminium (C). The unstable pyrrolinium (C) was prepared from oxalylation of the enamine of phenethylamine and ethyl 2-oxocyclopentanecarboxylate.

• 약학회지
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• 제38권5호
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• pp.544-554
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• 1994

Pyrrolidine-2,3-dione derivative A was synthesized from oxalylation of chiral enamine Ba. The stereostructure of its major diastereomer $(A_{maj})$ was determined as octahydro-2,3-dioxo-6aS-hyd roxy-1-(1S-methoxycarbonyl-2-phenylethyl)-cyclopenta[b]pyrrole-3aR-carboxylic acid ethyl ester Aa by means of NMR spectrum. This result implied that the asymmetric carbon-carbon bond forming reaction occurred preferentially at the ${\beta}-face$ of Ba.