Towards the total synthesis of aleurodiscal

被引:0
作者
Zhao, Hai-Xiao
Xu, Jing [1 ]
机构
[1] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
关键词
Total synthesis; Sesterterpenoids; Aleurodiscal; Cope rearrangement; trans-hydrindane; PALLADIUM-CATALYZED ALLYLATION; TRANSITION-METAL CATALYSIS; ASYMMETRIC TOTAL-SYNTHESIS; CARBON BOND FORMATION; (-)-RETIGERANIC ACID; ASTELLATOL; SESTERTERPENOIDS;
D O I
10.1016/j.tetlet.2023.154613
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aleurodiscal is one of the representative members of the isopropyl trans-hydrindane sesterterpenoid family. Herein, we describe our efforts towards the synthesis of a complex sesterterpenoid, aleurodiscal. The key precursor of the Cope rearrangement was concisely synthesized from a known bicyclic starting material in 13 linear steps. Our approach highlighted a Van Leusen homologation reaction and an oxida-tive rearrangement of a tertiary carbinol.& COPY; 2023 Elsevier Ltd. All rights reserved.
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页数:3
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共 41 条
[1]   A Concise Total Synthesis of (-)-HimalensineA [J].
Chen, Yuye ;
Hu, Jingping ;
Guo, Lian-Dong ;
Zhong, Weihe ;
Ning, Chengqing ;
Xu, Jing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (22) :7390-7394
[2]   Total synthesis of sesterterpenoids [J].
Chen, Yuye ;
Zhao, Jing ;
Lia, Shaoping ;
Xu, Jing .
NATURAL PRODUCT REPORTS, 2019, 36 (02) :263-288
[3]   TOTAL SYNTHESIS OF (+/-)-RETIGERANIC ACID [J].
COREY, EJ ;
DESAI, MC ;
ENGLER, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4339-4341
[4]   A COMPARISON OF (CHLOROMETHYL)ZINC AND (IODOMETHYL)ZINC CYCLOPROPANATION REAGENTS [J].
DENMARK, SE ;
EDWARDS, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :6974-6981
[5]   Total Synthesis of Daphniphyllum Alkaloids: From Bicycles to Diversified Caged Structures [J].
Guo, Lian-Dong ;
Chen, Yuye ;
Xu, Jing .
ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (11) :2726-2737
[6]   Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J [J].
Guo, Lian-Dong ;
Zhang, Yan ;
Hu, Jingping ;
Ning, Chengqing ;
Fu, Heyifei ;
Chen, Yuye ;
Xu, Jing .
NATURE COMMUNICATIONS, 2020, 11 (01)
[7]   Enantioselective Total Synthesis of (-)-Caldaphnidine O via a Radical Cyclization Cascade [J].
Guo, Lian-Dong ;
Hu, Jingping ;
Zhang, Yan ;
Tu, Wentong ;
Zhang, Yue ;
Pu, Fan ;
Xu, Jing .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (33) :13043-13048
[8]   Total Synthesis of Dapholdhamine B and Dapholdhamine B Lactone [J].
Guo, Lian-Dong ;
Hou, Jieping ;
Tu, Wentong ;
Zhang, Yan ;
Zhang, Yue ;
Chen, Louxi ;
Xu, Jing .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (29) :11713-11720
[9]   VARIECOLIN, A SESTERTERPENOID OF NOVEL SKELETON FROM ASPERGILLUS-VARIECOLOR MF138 [J].
HENSENS, OD ;
ZINK, D ;
WILLIAMSON, JM ;
LOTTI, VJ ;
CHANG, RSL ;
GOETZ, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3399-3403
[10]   Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides [J].
Hofstra, Julie L. ;
Poremba, Kelsey E. ;
Shimozono, Alex M. ;
Reisman, Sarah E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (42) :14901-14905