Studies directed towards the synthesis of immunosuppressive agent FK 506 : Synthesis of C-20 to C-27 moiety
โ Scribed by AV Rama Rao; T.K. Chakraborty; AV Purandare
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 202 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
An efficient approach has been developed to construct the entire TOP-HALF of FK-506 involving Grignard reaction of a C-28 bromide with a C-27 methylketo fragment.
The synthesis of the cyclohexyl moiety of FK-505 and its coupling reaction with the CIo-CZ6fragment to provide an advanced synthetic intermediate(Clo\_Cjq) are described,
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
The protected C(1) to C(15) segment of FK-506 has been prepared from D-glucose, glycolic and L-pipecolic acid. The novel, highly active immunosuppressive agent FK-506 (1) has attracted considerable attention.1 The biological potency as well as some unique structural features render this 23-membered