Synthetic studies on kinamycin antibiotics: elaboration of a highly oxygenated D-ring

The synthesis of the model compound of kinamycin antibiotics, which possesses correct relative configurations at C(1)C(4) on the D-ring, is reported. The key steps involve a Diels–Alder reaction of an indenone and a Danishefsky-type diene, and stereoselective construction of a tetraoxygenated D-ring.