化学
烯类反应
三萜
二羟基化
分子内力
萜烯
立体化学
羟醛反应
双环分子
四氧化锇
羟醛缩合
苯并呋喃
废止
有机化学
对映选择合成
催化作用
物理
病理
光学
替代医学
电子显微镜
医学
作者
Kinga Kuczynska,Jarosław Jaźwiński,Zbigniew Pakulski,Piotr Cmoch,Roman Luboradzki
标识
DOI:10.1021/acs.joc.1c00697
摘要
cis-Dihydroxylation of trinor-18α-olean-17(22)-ene 2 with osmium tetroxide led to diol 9. Its cleavage with lead tetraacetate gave tetracyclic ketoaldehyde 10. By comparison, the ozonation of trinor-18α-olean-17(22)-ene 2 in the presence of p-toluenesulfonic acid gave the corresponding ketoacetal 12. Both products were subjected to an intramolecular aldol reaction under the acidic conditions and yielded unusual triterpenes bearing a bicyclo[4.3.1]decane fragment (22). Further manipulation of the protective groups afforded compounds useful in triterpene synthesis, especially in the preparation of potentially biologically active saponins based on a tetracyclic terpene core.
科研通智能强力驱动
Strongly Powered by AbleSci AI