Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization

Xie, Sujun1,2,3; Chen, Yuye1,2,3; Zhang, Yan1,2,3; Zhang, Zhiting1,2,3; Hu, Xinyue1,2,3; Yan, Chongyuan1,2,3; Xu, Jing1,2,3

2024-03-20

10.1016/j.xcrp.2024.101855

CELL REPORTS PHYSICAL SCIENCE   影响因子和分区

2666-3864

The fusicoccane diterpenoids have triggered particular interest from the organic synthesis community in recent years, owing to their promising biological profiles and complex chemical structures. Here, we report collective, asymmetric total syntheses of five fusicoccane diterpenoids, namely fusicoauritone, fusicogigantones A and B, fusicogigantepoxide, and anadensin. This work features a Yu [5+2+1] cycloaddition that is shown to be a swift approach to access the [5,8] -bicyclic ring system and an oxidative Nazarov cyclization that facilely fabricated the critical cyclopentenone moiety via an unfunctionalized tertiary divinyl carbinol (TDC) substrate. The substrate scope study of the oxidative Nazarov cyclization also revealed a general and robust transformation that is capable of synthesizing highly substituted cyclopentenones via unfunctionalized TDCs.

SCI

英语

第一 ; 通讯

NSFC["21971104","22001114","22271136"] ; Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis[ZDSYS20190902093215877] ; Shenzhen Science and Technology Innovation Commission[JCYJ20220814203252001] ; Guangdong Provincial Key Laboratory Of Catalysis[2020B121201002] ; Guangdong Innovative Program[2019BT02Y335] ; Key research projects in colleges and universities in Guangdong Province[2021ZDZX2035] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17783101] ; Innovative Team of Universities in Guangdong Province[2020KCXTD016]

Chemistry ; Energy & Fuels ; Materials Science ; Physics

Chemistry, Multidisciplinary ; Energy & Fuels ; Materials Science, Multidisciplinary ; Physics, Multidisciplinary

WOS:001258485500001

CELL PRESS

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Dept Chem,Guangdong Prov Key Lab Catalysis, Shenzhen Key Lab Small Mol Drug Discovery & Synth, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis & Shenzhen, Key Lab Small Mol Drug Discovery & Synth, Shenzhen 518055, Peoples R China

Xie, Sujun,Chen, Yuye,Zhang, Yan,et al. Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization[J]. CELL REPORTS PHYSICAL SCIENCE,2024,5(3).

Xie, Sujun.,Chen, Yuye.,Zhang, Yan.,Zhang, Zhiting.,Hu, Xinyue.,...&Xu, Jing.(2024).Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization.CELL REPORTS PHYSICAL SCIENCE,5(3).

Xie, Sujun,et al."Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization".CELL REPORTS PHYSICAL SCIENCE 5.3(2024).