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
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.
📜 SIMILAR VOLUMES
## Abstract The total synthesis of the tetrahydroisoindolinone moiety corresponding to proxiphomin (**1**) is described, bearing functional groups for the attachment of the macrocyclic ring. __Knoevenagel‐Cope__ condensation of racemic 2‐(benzyloxycarbonyl‐amino)‐3‐phenylpropanal (**2**) with methy
## Abstract A general scheme for the synthesis of the tetrahydroisoindolinone moiety of naturally occurring cytochalasans and unnatural analogs was developed. The key‐step consists of the __inter__molecular [2+4]cycloaddition of 4‐methylsorbinol (7) to an alkylidene malonic ester derivative such as
## Abstract The bicycle aldehyde **7** was prepared from the hydroxy ester **3** for the attachment of teh macrocyclic moiety of the cytochalasans. To protect the C(6),C(7)‐double bond the intermediates **8**, **9** and **13** were transformed into the epoxides **10**, **11** and **14**, respective
## 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