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Studies directed towards the synthesis of immunosuppressive agent FK-506: synthesis of the entire top-half

โœ Scribed by A.V. Rama Rao; T.K. Chakraborty; D Sankaranayanan; A.V. Purandare

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
225 KB
Volume
32
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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.

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Synthetic studies on the immunosuppressive agent FK-506: Enantioselective synthesis of a C22๎—ธC34 fragment
โœ Robert K. Baker; Kathleen M. Rupprecht; David M. Armistead; Joshua Boger; Robert ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 257 KB

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