Short and efficient enantioselective total synthesis of angucyclinone type antibiotics (+)-rubiginone B2 and (+)-ochromycinone

Abstract

The enantioselective total synthesis of antibiotics rubiginone B₂ and ochromycinone is achieved from enantiopure (S)-5-methoxy-2-(p-tolylsulfinyl)-1,4-naphthoquinone and a racemic vinylcyclohexene through a short sequence involving a tandem Diels–Alder reaction–sulfoxide elimination process with simultaneous kinetic resolution of the racemic diene, followed by controlled aromatization and functional group deprotection.