Chemistry of 1,5-diketone derivatives. 1. Oxidation of 8a-methoxy-4a,5,6,7,8,8a-hexahydrochromenes by monoperphthalic acid

Abstract

2-(2-Oxo-3-hydroxy-1,3-diphenylpropyl)cyclohexanone, 2-(2,3-dioxo-1,3-diphenylpropyl)cyclohexanone, and 2-benzyl-7a-hydroxy-3-phenylperhydrobenzofuran are formed by the action of monoperphthalic acid on 8a-methoxy-2,4-diphenyl-4a,5,6,7,8,8a-hexahydrochromene. Under analogous conditions, 4a-methoxy-10-phenyl-1,2,3,4, 4a,6,7,8,9,10a-decahydroxanthene forms 7a-hydroxy-3-phenyloctahydrobenzo[b]furan-2-spiro-1′-cyclohexan-2′-one and its dehydration product. The behavior of the compounds obtained toward acetic anhydride and a methanolic solution of HCl was studied. The configurations of the reaction products and the reaction path are considered.