Asymmetric total synthesis of (+)-astellatol and (-)-astellatene

Zhao, Nan1,2; Xie, Shengling1,2; Tian, Peilin1,2; Tong, Rongbiao3; Ning, Chengqing1,2,4; Xu, Jing1,2

2019-06-21

10.1039/c9qo00384c

Organic Chemistry Frontiers   影响因子和分区

2052-4129

The chemical structure of isopropyl trans-hydrindane sesterterpenoids features a highly substituted trans-hydrindane moiety that holds an isopropyl or isopropenyl group at the segment to the right and a congested polycyclic ring system at the segment to the left, therefore representing formidable challenges for their synthesis. Here, we wish to describe the full account of our synthesis of (+)-astellatol, as well as the first total synthesis of (-)-astellatene. Our work highlights a mercury(ii)-catalyzed Grignard reaction, an intramolecular Pauson-Khand reaction, a samarium(ii)-mediated reductive radical 1,6-addition and a novel strategy for the synthesis of highly substituted trans-hydrindane natural products.

SCI ; EI ; IC

英语

第一 ; 通讯

SZSTI[JCYJ20170817110515599] ; SZSTI[KQJSCX20170728154233200]

Chemistry

Chemistry, Organic

WOS:000473641300012

ROYAL SOC CHEMISTRY

20192407053744

Samarium compounds ; Synthesis (chemical)

Chemical Reactions:802.2

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen, Peoples R China
3.Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Clear Water Bay, Hong Kong, Peoples R China
4.SUSTech Acad Adv Interdisciplinary Studies, Shenzhen, Peoples R China

Zhao, Nan,Xie, Shengling,Tian, Peilin,et al. Asymmetric total synthesis of (+)-astellatol and (-)-astellatene[J]. Organic Chemistry Frontiers,2019,6(12):2014-2022.

Zhao, Nan,Xie, Shengling,Tian, Peilin,Tong, Rongbiao,Ning, Chengqing,&Xu, Jing.(2019).Asymmetric total synthesis of (+)-astellatol and (-)-astellatene.Organic Chemistry Frontiers,6(12),2014-2022.

Zhao, Nan,et al."Asymmetric total synthesis of (+)-astellatol and (-)-astellatene".Organic Chemistry Frontiers 6.12(2019):2014-2022.