Total Synthesis of (±)-4,5-Bis-epi-Neovibsanin A and B: A Neurite Outgrowth Comparison Study

被引：20

作者：

Chen, Annette P-J. ^{[1
]}

Mueller, C. Catharina ^{[2
]}

Cooper, Helen M. ^{[2
]}

Williams, Craig M. ^{[1
]}

机构：

[1] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld 4072, Australia

[2] Univ Queensland, Queensland Brain Inst, Brisbane, Qld 4072, Australia

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 16期

基金：

澳大利亚研究理事会;

关键词：

VIBSANE-TYPE DITERPENES; VIBURNUM-AWABUKI; CONSTRUCTION; CORE; (+/-)-5,14-BIS-EPI-SPIROVIBSANIN-A; (+/-)-JIADIFENIN; FURANOVIBSANIN; NEOVIBSANINS; CHEMISTRY;

D O I：

10.1021/ol901406j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-4,5-Bis-epi-neovibsanin A and B were synthesized in 12 steps. The acid-catalyzed, one-pot, five-step cascade reaction was central toward the formation of the tricyclic core. The two diastereomers of natural neovibsanin A and B acted as desirable derivatives for structure-activity relationship studies to probe neurotrophic activity. Both (+/-)-4,5-bis-epi-neovibsanin A and B strongly potentiate neurite outgrowth in NGF-stimulated PC12 cells. Furthermore, the tricyclic core appears to be largely responsible for promoting a biological response.

引用

页码：3758 / 3761

页数：4

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