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Approaches to the Synthesis of Cytochalasans. Part 2. Pyrrolinone derivatives as basic units

✍ Scribed by Tibur Schmidlin; Christoph Tamm


Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
632 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

Several attempts to prepare 3‐acetyl‐5‐benzyl‐3‐pyrrolin‐2‐one (7) from phenylalanine are described. This goal was only reached formally, because compound 7 exists in the tautomeric form of (Z)‐5‐benzyl‐3‐(1′‐hydroxyethylidene)‐4‐pyrrolin‐2‐one (17) according to the spectral data. The problem of tautomerism in pyrrolinone systems is discussed.


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Starting from D-glutamic acid (5), the bicyclic compounds 4a and 4b were synthesized via 17 (Schemes 1 and 2). The reaction leading to 4g and 4h with LiCuPhz was not successful. But treatment of the N-protected model lactams 19,21, and 22 with Li,Cu(CN)Ph, gave the amino ketones 24,26, and 27, respe

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## Abstract The stereo‐ and regiochemical course in the [2+4]cycloaddition of the chiral alkylidene malonic ester **1** to selected derivatives of (2__E__, 4__E__)‐4‐methyl‐2, 4‐hexadien‐l‐ol (**2**) and (2__E__, 4__E__)‐4‐methyl‐2, 4‐hexadien‐l‐al (**12**) has been investigated. The results are di