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

✍ Scribed by A.F Barrero; J.E Oltra; A Barragán

• Book ID: 104226578
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 276 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)94502-7

✦ Synopsis

From natural 14-hydroxy-Q-epi-P-caryophyllene (11, 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 HCPBA, epoxides 7 and Q were obtained. The rigid conformation of 7 and Q allowed us to establish their skeleton and cis interannular junction. Thus, the proposed structure for 1 was confirmed.

In our laboratory, a new natural sesquiterpene alcohol, 14-hydroxy-9epi-P-caryophyllene Cl), which was a mixture of two conformational isomers (la, lb) at room temperature, has been recently isolated Cl]. Treatment of 1 with Ac,O and Py yielded the acyl derivative 2 [23 (table l), while