Synthetic studies on the immunosuppressive agent FK-506: Construction of the polycarbonyl region
โ Scribed by Kathleen M. Rupprecht; Robert K. Baker; Joshua Boger; Alita A. Davis; Paul J. Hodges; Joanne F. Kinneary
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 263 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
The C28-C32 cyclohexyl group of the natural product, FK-506, was prepared enantioselectively from the iodolactor~ by replacement of iodide with retention of configuration. The C27-C28 trisubstituted olefin was introduced stereoselectively via a classical aldol/elimination sequence employing titanium
Beckmann rearrangement of FK506 E-oxime gave amide 2 and the fragmentation product 4. Compound 4 was atso prepared by total synthesis. The immunosuppressant FK506 has been the subject of considerabie synthetic' and degradative2 studies. As part of our pmgramme in this area we investigated the stNdU