Organometallic additions to protected quinone bis-epoxides and quinone monoacetals: synthesis of the aranorosin nucleus

Abstract

The addition reactions of organometallic reagents to monoprotected quinone bis-epoxides 7 and quinone monoacetals 5 provide a route to the highly oxygenated cyclohexanols 2 and 3; the application of this methodology to the preparation of the aranorosin analogue 4 is described.