13-Step Total Synthesis of Atropurpuran

Xie, Shengling; Chen, Gui; Yang, Hao; Hou, Jieping; He, Yongping; Zhao, Tongyun; Xu, Jing1

2019-02-27

10.1021/jacs.9b00391

Journal of the American Chemical Society   影响因子和分区

0002-7863

Herein, we report a concise total synthesis of atropurpuran, a unique and synthetically challenging pentacyclic diterpene that bears a tetracyclo-[5.3.3.0(4,9).0(4,12)]-tridecane skeleton that is unprecedented among natural terpenes. This 13-step approach features a strategy that include early stage rapid skeleton formation and the late-stage introduction of reactive functional groups, thus allowed a high overall synthetic efficiency with minimal use of PGs. The key transformations of our work include a facile construction of the spiro[5.5]-undecane moiety through an ring-closing enyne metathesis reaction and an efficient formation of the tetracyclo[5.3.3.0(4,9).0(4,12)]-tridecane scaffold via an regio-selective double oxidative dearomatization/intramolecular Diels-Alder reaction cascade. This efficient approach should also inspire further advances in the synthesis of related complex diterpenes and diterpenoid alkaloids.

SCI ; EI ; IC

英语

NI期刊

通讯

Shenzhen Nobel Prize Scientists Laboratory Project[C17783101]

Chemistry

Chemistry, Multidisciplinary

WOS:000460200100021

AMER CHEMICAL SOC

20191006585684

Musculoskeletal system ; Scaffolds

Construction Equipment:405.1 ; Biomechanics, Bionics and Biomimetics:461.3 ; Chemical Reactions:802.2

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China

Xie, Shengling,Chen, Gui,Yang, Hao,et al. 13-Step Total Synthesis of Atropurpuran[J]. Journal of the American Chemical Society,2019,141(8):3435-3439.

Xie, Shengling.,Chen, Gui.,Yang, Hao.,Hou, Jieping.,He, Yongping.,...&Xu, Jing.(2019).13-Step Total Synthesis of Atropurpuran.Journal of the American Chemical Society,141(8),3435-3439.

Xie, Shengling,et al."13-Step Total Synthesis of Atropurpuran".Journal of the American Chemical Society 141.8(2019):3435-3439.