Yang,YR (reprint author),Chinese Acad Sci,Kunming Inst Bot,State Key Lab Phytochem & Plant Resources West Ch,Kunming 650201,Peoples R China.
The collective total synthesis of tetracyclic diquinane Lycopodium alkaloids, (+)-paniculatine, (-)-magellanine, (+)-magellaninone, and two analogues (-)-13-epi-paniculatine and (+)-3-hydroxyl-13-dehydro-paniculatine, has been accomplished. By logic-guided addition of a strategically useful hydroxyl group at C-3 of paniculatine, the formidable tetracyclic core was rapidly synthesized utilizing a site-specific and stereoselective aldol cyclization, thus making the ABD -> ABCD tetracyclic approach to diquinane Lycopodium alkaloids attainable for the first time.
1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100039, Peoples R China
Jiang,Shi-Zhi;Lei,Ting;Wei,Kun;Yang,Yu-Rong.Collective Total Synthesis of Tetracyclic Diquinane Lycopodium Alkaloids (+)-Paniculatine, (-)-Magellanine, (+)-Magellaninone and Analogues Thereof,ORGANIC LETTERS,2014,156():147-154