Absolute configuration of cembrane diterpenoids from Bursera multijuga.

Natural product communications

PubMedID: 25918784

Hernández-Hernández JD, García-Gutiérrez HA, Román-Marín LU, Torres-Blanco YI, Cerda-García-Rojas CM, Joseph-Nathan P. Absolute configuration of cembrane diterpenoids from Bursera multijuga. Nat Prod Commun. 2014;9(9):1249-52.
The stems of Bursera multijuga afforded (-)-(1S,3E,7R,8R,11E)-7,8-epoxycembra-3,11-dien-1-ol (1) and its acetate 2, together with cembrene A (3), nephthenol (4), and cembrenol (5). The structures of 1 and 2 were elucidated by 1D and 2D NMR, HRESIMS, and X-ray diffraction. The conformational preference of flexible 1 was studied by molecular modeling at the DFT B3LYP/DGDZVP level of theory. Good agreement between calculated and experimental vibrational circular dichroism curves established the absolute configuration of 1. This is the first time that cembrane derivatives have been isolated from the genus Bursera.