Synthesis of the Tricyclic Caged Core of Palhinine Alkaloids Based on a Non-Diels-Alder-Type Strategy

被引:7
作者
Lu, Shi-Chao
Liang, Yu-Yan
Li, Liang [2 ,3 ]
Wang, Xiao-Lei
Zhang, Shi-Peng
Gong, Ya-Ling
Xu, Shu [1 ]
机构
[1] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, 2A NanWei Rd, Beijing 100050, Peoples R China
[2] Nankai Univ, Coll Pharm, State Key Lab Med Chem Biol, Haihe Educ Pk 38,Tongyan Rd, Tianjin 300350, Peoples R China
[3] Nankai Univ, Tianjin Key Lab Mol Drug Res, Haihe Educ Pk 38,Tongyan Rd, Tianjin 300350, Peoples R China
基金
中国国家自然科学基金; 北京市自然科学基金;
关键词
LYCOPODIUM ALKALOIDS; RING-SYSTEM; CONSTRUCTION;
D O I
10.1021/acs.orglett.9b01898
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise synthesis of the tricyclo[4.3.1.0(3,7)]decane caged core of palhinine alkaloids was developed with SmI2-mediated cyclization and light-initiated radical addition-fragmentation as key steps. Compared with the reported racemic routes which are all based on Diels-Alder-type key reactions, our strategy would be more readily accessible to the asymmetric total syntheses of the palhinine alkaloids.
引用
收藏
页码:5567 / 5569
页数:3
相关论文
共 21 条
[1]   Benzylic and Allylic Oxidations with Bis(trifluoroacetoxyiodo)benzene and tert-Butyl Hydroperoxide [J].
Catir, Mustafa ;
Kilic, Hamdullah .
SYNLETT, 2010, (09) :1319-1322
[2]   Biomimetic Syntheses of (±)-Isopalhinine A, (±)-Palhinine A, and (±)-Palhinine D [J].
Chen, Chih-Ming ;
Shiao, Hui-Yi ;
Uang, Biing-Jiun ;
Hsieh, Hsing-Pang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (47) :15572-15576
[3]   PYRIDINE-DERIVED TRIFLATING REAGENTS - AN IMPROVED PREPARATION OF VINYL TRIFLATES FROM METALLO ENOLATES [J].
COMINS, DL ;
DEHGHANI, A .
TETRAHEDRON LETTERS, 1992, 33 (42) :6299-6302
[4]   Isopalhinine A, a Unique Pentacyclic Lycopodium Alkaloid from Palhinhaea cernua [J].
Dong, Liao-Bin ;
Gao, Xiu ;
Liu, Fei ;
He, Juan ;
Wu, Xing-De ;
Li, Yan ;
Zhao, Qin-Shi .
ORGANIC LETTERS, 2013, 15 (14) :3570-3573
[5]   Efficient construction of the A/C/D tricyclic skeleton of palhinine A [J].
Duan, Shuangshuang ;
Long, Dan ;
Zhao, Changgui ;
Zhao, Gaoyuan ;
Yuan, Ziyun ;
Xie, Xingang ;
Fang, Jianguo ;
She, Xuegong .
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (09) :1137-1143
[6]   Approach to the Core Structure of the Polycyclic Alkaloid Palhinine A [J].
Gaugele, Dominik ;
Maier, Martin E. .
SYNLETT, 2013, 24 (08) :955-958
[7]   A NEW SEQUENCE FOR THE SYNTHESIS OF 3-(POLY)ENOYLTETRAMIC ACIDS [J].
JONES, RCF ;
TANKARD, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :240-241
[8]   A 3 COMPONENT FREE-RADICAL COUPLING REACTION - VICINAL DIALKYLATION OF ALPHA,BETA-UNSATURATED KETONES AND ESTERS [J].
KECK, GE ;
KORDIK, CP .
TETRAHEDRON LETTERS, 1993, 34 (43) :6875-6876
[9]   SYNTHESIS OF THE ENANTIOMERS OF 4-VINYLCYCLOHEXENE [J].
MASH, EA ;
GREGG, TM .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6180-6182
[10]   Heathcock-Inspired Strategies for the Synthesis of Fawcettimine-Type Lycopodium Alkaloids [J].
Murphy, Rebecca A. ;
Sarpong, Richmond .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (01) :42-56