Formal Total Synthesis of Oximidine II via a Suzuki-Type Cross-Coupling Macrocyclization Employing Potassium Organotrifluoroborates

摘要: A formal total synthesis of oximidine II has been achieved, employing a Suzuki-type coupling approach to construct the highly strained, polyunsaturated 12-membered macrolactone. To achieve this goal, benefit was derived from stability potassium alkenyltrifluoroborates establish conditions for macrocyclization. The stereocontrolled formation cis-1,2-diol subunit accomplished using diastereoselective, reagent controlled addition chiral aldehyde utilizing Carreira protocol. Advantage taken Snieckus hydroborating gain access key trifluoroborate needed