title: Collective Total Syntheses of Atisane-Type Diterpenes and Atisine-Type Diterpenoid Alkaloids: (±)-Spiramilactone B, (±)-Spiraminol, (±)-Dihydroajaconine, and (±)-Spiramines C and D.
abstract: The first total syntheses of the architecturally complex atisane-type diterpenes and biogenetically related atisine-type diterpenoid alkaloids (±)-spiramilactone B, (±)-spiraminol, (±)-dihydroajaconine, and (±)-spiramines C and D are reported. Highlights of the synthesis include a late-stage biomimetic transformation of spiramilactone B, a facile formal lactone migration from the pentacyclic skeleton of spiramilactone E, a highly efficient and diastereoselective 1,7-enyne cycloisomerization to construct the functionalized tetracyclic atisane skeleton, and a tandem retro-Diels-Alder/intramolecular Diels-Alder sequence to achieve the tricyclo[6.2.2.0] ring system.
authors.affiliation: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041 (P. R. China).
authors.forename: Hang
authors.initials: H
authors.lastname: Cheng
authors.affiliation: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041 (P. R. China).
authors.forename: Fan-Hao
authors.initials: FH
authors.lastname: Zeng
authors.affiliation: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041 (P. R. China).
authors.forename: Xue
authors.initials: X
authors.lastname: Yang
authors.affiliation: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041 (P. R. China).
authors.forename: Yin-Juan
authors.initials: YJ
authors.lastname: Meng
authors.affiliation: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041 (P. R. China). liangxu@scu.edu.cn.
authors.forename: Liang
authors.initials: L
authors.lastname: Xu
authors.affiliation: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041 (P. R. China).
authors.forename: Feng-Peng
authors.initials: FP
authors.lastname: Wang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D004224:Diterpenes; D006576:Heterocyclic Compounds, 4 or More Rings; C000610603:spiramilactone B; C000592452:spiramine C; C000592453:spiramine D; C000610604:spiraminol
keywords: alkaloids; cycloisomerization; ruthenium; terpenoids; total synthesis