Tetrahedron Letters p. 229 - 232 (1998)
Update date:2022-07-29
Topics:
Baker, Robert K.
Rupprecht, Kathleen M.
Armistead, David M.
Boger, Joshua
Frankshun, Robert A.
Hodges, Paul J.
Hoogsteen, Karst
Pisano, Judith M.
Witzel, Bruce E.
The C28-C32 cyclohexyl group of the natural product, FK-506, was prepared enantioselectively from the iodolactone by replacement of iodide with retention of configuration. The C27-C28 trisubstituted olefin was introduced stereoselectively via a classical aldol/elimination sequence employing titanium enolate methodology. Elaboration of this chemistry has led to a synthesis of a C22-C34 fragment of the natural product.
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