Synthesis of the tricyclic skeleton of Daphniphyllum alkaloids daphnimacropodines

Chen，Yuye1; Guo，Lian Dong1; Xu，Jing1,2

2021-05-11

10.1016/j.tetlet.2021.153030

TETRAHEDRON LETTERS   影响因子和分区

0040-4039

1873-3581

Owing to their interesting biological activity and architectural complexity, Daphniphyllum alkaloids have triggered intensive research activities from the synthetic community. Nine types of Daphniphyllum alkaloids, such as daphniphylline-type, daphmanidin A-type, calyciphylline A-type, and yuzurimine-type alkaloids, have been accessed by total synthesis over past decades. However, more than twenty types of Daphniphyllum alkaloids remain inaccessible by chemical synthesis. Here, we wish to describe our recent efforts toward the total synthesis of daphniglaucin-C type alkaloids, namely, daphnimacropodines. Key features of our synthesis include a Robinson annulation and a Simmons-Smith cyclopropanation that constructed the pivotal vicinal quaternary centers, and a Horner-Wadsworth-Emmons reaction that forms the critical cyclopentene motif.

Daphniglaucin C Daphnimacropodines Daphniphyllum alkaloids Natural products Total synthesis

SCI

英语

第一 ; 通讯

Shenzhen Science and Technology Innovation Committee["ZDSYS20190902093215877","JCYJ20170817110515599","KQTD20150717103157174"] ; Shenzhen Bay Laboratory[SZBL2019062801006] ; NSFC[21772082,21971104,22001114] ; Guangdong Innovative Program[2019BT02Y335] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Innovative Team of Universities in Guangdong Province[2020KCXTD016] ; China Postdoctoral Science Foundation[2020M672689]

Chemistry

Chemistry, Organic

WOS:000646579300012

PERGAMON-ELSEVIER SCIENCE LTD

CHEMISTRY

2-s2.0-85104112868

Scopus

1.Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis and Department of Chemistry and Shenzhen Grubbs Institute and Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
2.Shenzhen Bay Laboratory,Shenzhen,518132,China

Chen，Yuye,Guo，Lian Dong,Xu，Jing. Synthesis of the tricyclic skeleton of Daphniphyllum alkaloids daphnimacropodines[J]. TETRAHEDRON LETTERS,2021,71.

Chen，Yuye,Guo，Lian Dong,&Xu，Jing.(2021).Synthesis of the tricyclic skeleton of Daphniphyllum alkaloids daphnimacropodines.TETRAHEDRON LETTERS,71.

Chen，Yuye,et al."Synthesis of the tricyclic skeleton of Daphniphyllum alkaloids daphnimacropodines".TETRAHEDRON LETTERS 71(2021).