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FK-506 synthetic studies. 3. An efficient asymmetric synthesis of the C(24)–C(34) fragment of FK-506, FR-900520, and FR-900523

✍ Scribed by Amos B. Smith III; Karl J. Hale; Leif M. Laakso; Kwunmin Chen; Antoni Riéra


Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
276 KB
Volume
30
Category
Article
ISSN
0040-4039

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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