Evidences about the stereochemistry of 14-hydroxy-9-epi-β-caryophyllene

Article abstract of DOI:10.1016/S0040-4039(00)94502-7

From natural 14-hydroxy-9-epi-β-caryophyllene (1), the acyl derivatives 2 and 3 were prepared. These compounds appeared as a mixture of two conformational isomers (7/3). When 1 was oxidized with MCPBA, epoxides 7 and 9 were obtained. The rigid conformation of 7 and 9 allowed us to establish their skeleton and cis interannular junction. Thus, the proposed structure for 1 was confirmed.