Short syntheses of (−)-clavaminol A and deacetyl (+)-clavaminol H

Abstract

Concise stereoselective syntheses of (−)-clavaminol A and deacetyl (+)-clavaminol H have been achieved from simple starting materials. Highlights of the synthesis for (−)-clavaminol A include a highly diastereoselective chelation-controlled hydride reduction of an amino ketone to give the anti amino alcohol directly, and NaBH4-mediated dehalogenation. The main synthetic approach for deacetyl (+)-clavaminol H features a highly diastereoselective chelation-controlled hydride reduction of the amino ketone to construct the anti amino alcohol and a palladium catalyzed hydrogenation reaction at the final step.