A synthetic route to the title ring system is described, which starts from isatoic anhydride and allylamines, and involves as the key step an intramolecular nitrile imine cycloaddition. The simultaneous formation of two new rings, often accompanied by a high degree of regio-and stereo-selectivity, m
The intramolecular nitrile oxide-olefin [3+2] cycloaddition route to the maytansinoids
โ Scribed by Pat N. Confalone; Soo S. Ko
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 223 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The macrocyclisation of the olefinic nitrile oxide 24 to the ansa-macrolide skeleton 26, a model for a novel approach to the maytansinoids. is described.
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## Abstract The readily available alkyl dicyanoacetates 1 reacted with the 1,3โdipolar reagents arenecarbonitrile oxides 2โฒ and arenecarbonitrile imines 5โฒ to afford 1,2,4โoxadiazol and 1,2,4โtriazol derivatives. The arenecarbonitrile oxides 2โฒ with electronโdonating groups on the arene ring gave p
A general method is described to prepare pyrazolo [3,4-g]-[2,1]dihydrobenzoisoxazol(in)es utilizing intramolecular nitrile oxide cycloaddition (INOC) as the key step. ยฉ1999El~vierScienceLtd. Allfi~ ~serv~.