Studies on the synthesis of the inostamycin natural products: a reductive aldol/reductive Claisen approach to the C10-C24 ketone fragment.
[reaction: see text] An approach to the C10-C24 ketone fragment of the inostamycin family of polyether antibiotics is described. The synthetic strategy utilizes an asymmetric Rh-catalyzed reductive aldol reaction and a stereoselective Rh-catalyzed reductive Claisen rearrangement as the key steps in formation of alkene and vinyl iodide synthons, respectively.
Fuller
Nathan O
NO
Department of Chemistry, Venable and Kenan Laboratories, University of North Carolina at Chapel Hill, 27599-3290, USA.
Morken
James P
JP
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000900:Anti-Bacterial Agents; D005663:Furans; D007659:Ketones; C071861:inostamycin