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http://nopr.niscpr.res.in/handle/123456789/16636| Title: | Novel derivatives of ascomycin through photochemistry |
| Authors: | Bulusu, Murty A R C Haidl, Ewald Schulz, Gerhard Waldstatten, Peter Grassberger, Maximilian |
| Issue Date: | Oct-1999 |
| Publisher: | NISCAIR-CSIR, India |
| Abstract: | Irradiation of ascomycin 1 leads to three reaction pathways: (a) [1,3]-sigmatropic shift of the allylic carbonyl group leading to the ring-contracted products 3 and 4, (b) electron-transfer from the amide nitrogen to the carbonyl group followed by reorganisation leading to a zwitterionic intermediate Z which undergoes either intramolecular cyclisation (leading to. 6 in CH3CN) or addition of methanol (leading to 2 in MeOH), and, (c) decarbonylative fragmentation resulting in the acyclic lactone 5. The effects of solvent, wavelength, and the substrate-srtucture on the product distribution have been examined. Simple transformations of the photoproducts leading to novel derivatives are presented. |
| Page(s): | 1159-1164 |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Appears in Collections: | IJC-B Vol.38B(10) [October 1999] |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 38B(10) 1159-1164.pdf | 1.17 MB | Adobe PDF | View/Open |
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