Department of Chemistry, Williams College, 01267-2092, Williamstown, Massachusetts.
J Chem Ecol. 1991 Mar;17(3):663-85. doi: 10.1007/BF00982134.
Originally isolated fromDipterocarpus kerrii, the two previously uncharacterized sesquiterpenes,1 and20, were synthesized from α-gurjunene. A novel process involvingm-chloroperoxybenzoic acid oxidation ofα-gurjunene produced20 in one step. Spectroscopic studies determined that the diene moiety in20 is nonconjugated and also found the C-4 tertiary alcohol center to have theα-configuration, while the other stereocenters have configurations matching the corresponding centers inα-gurjunene. Bioassays with termites demonstrated that20 was more toxic than1, resulting in a 50% mortality in seven days when offered toNeotermes ?dalbergiae on filter papers. The chemicals appear to result from biotransformation ofα-gurjunene. In view of its similarity to the known sesquiterpeneγ-gurjunene, we suggest that20 be referred to asγ-gurjunenol.
最初从龙脑香科坡垒中分离得到的两种以前未被描述的倍半萜烯 1 和 20,是由α-古巴烯合成得到的。一个涉及间氯过氧苯甲酸氧化α-古巴烯一步法生成 20 的新方法。光谱研究确定 20 中的二烯部分是非共轭的,还发现 C-4 叔醇中心具有α-构型,而其他的手性中心与α-古巴烯中相应的中心具有相同的构型。用白蚁进行的生物测定表明,20 比 1 毒性更大,当用滤纸提供给黄胸散白蚁时,七天内死亡率达到 50%。这些化学物质似乎是α-古巴烯生物转化的结果。鉴于它与已知的倍半萜γ-古巴烯相似,我们建议将 20 称为γ-古巴烯醇。