7517-02-4Relevant articles and documents
A two-directional approach to a (-)-dictyostatin C11-C23 segment: Development of a highly diastereoselective, kinetically-controlled Meerwein-Ponndorf-Verley reduction
Dilger, Andrew K.,Gopalsamuthiram, Vijay,Burke, Steven D.
, p. 16273 - 16277 (2008/09/20)
A three-step synthesis of a precursor to the C11-C23 segment of (-)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels-Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, followed by a novel, highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of the hydropyranone subunits under kinetic control to yield the bis-(axial alcohol) 4. Generalized studies of both the HDA and MPV methodologies are also described.