Studies toward the total synthesis of hibarimicinone. Progress on the assembly of the AB- and GH-ring systems

Studies directed towards the synthesis of the AB- and GH-ring systems of hibarimicinone are described. The synthesis of tetralin was accomplished in three steps (43% overall yield) from benzoquinone and resolved using a Lipase-mediated resolution to >92% ee. Key reactions developed en route to the AB/GH ring systems of hibarimicinone include a dimethyl dioxirane oxidation for stereocontrolled introduction of the C(14) and C(14′) hydroxyl groups and the stereoselective addition of a n-propylcerium dichloride to ketone to give diol .