Conformationally selective transannular cyclizations of humulene 9,10-epoxide. Synthesis of the two skeletally different cyclohumulanoids: dl-bicyclohumulenone and dl-africanol
摘要:
Two cyclohumulanoids, dl-bicyclohumulenone ( 4) and dl-africanol ( 7 were synthesized through newly developed conformationally selective transannular cyclization of humulene 9,10-epoxide ( 2). The epoxide 2 was converted to a bicyclohumulenediol diacetate 3a in 70% yield by treatment with BF 3·OEt 2-Ac 2O, while treatment of 2 with trimethylsilyl trifluoromethansulfonate gave an africen-10-ol ( 5a and 5b) in 80% yield. The two intermediates 3a and 5a furnished the natural products 4 and 7 in 30 and 8 % yield from 2 respectively.
展开
DOI:
10.1016/0040-4039(80)80152-3
被引量:
年份:
1980
通过文献互助平台发起求助,成功后即可免费获取论文全文。
相似文献
参考文献
引证文献
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用!