Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2019; 51(08): 1825-1831
DOI: 10.1055/s-0037-1611713
DOI: 10.1055/s-0037-1611713
paper
Efficient Synthesis of Several Natural Oligostilbenes from the Biomimetic Oxidation of Brominated Isorhapontigenin
This research work was financially supported by the National Natural Science Foundation of China (No. 21462024).Further Information
Publication History
Received: 30 October 2018
Accepted after revision: 06 December 2018
Publication Date:
23 January 2019 (online)
Abstract
This study extensively investigated the regioselective oxidative coupling reactions of 5-bromoisorhapontigenin catalyzed by FeCl3·6H2O or HRP/H2O2 in different solvent systems and the distinct reductive debromination of the isolated dimeric coupling intermediates. Natural (±)-bisisorhapontigenin A and (±)-lehmbachol A and B were efficiently prepared. (±)-Gnetuhainin I, (±)-gnemontanin E, (±)-7-O-ethylgnetuhainin I, and (±)-gnemontanin F were synthesized for the first time.
Key words
isorhapontigenin - oligostilbenes - regioselectivity - biomimetic synthesis - oxidative coupling - debrominationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611713.
- Supporting Information
-
References
- 1a Lin M, Yao CS. Stud. Nat. Prod. Chem. 2006; 33: 601
- 1b Shen T, Wang XN, Lou HX. Nat. Prod. Rep. 2009; 26: 916
- 1c Kawazoe K, Shimogai N, Takaishi Y, Rao KS, Imakura Y. Phytochemistry 1997; 44: 1569
- 1d Zhai Y.-M, Jiang K, Qu S.-J, Luo H.-F, Tan J.-J, Tan C.-H. RSC Adv. 2016; 6: 50083
- 1e Huang K.-S, Wang Y.-H, Li R.-L, Lin M. Phytochemistry 2000; 54: 875
- 2a Velu SS, Thomas NF, Weber JF. Curr. Org. Chem. 2012; 16: 605
- 2b Snyder SA, Elsohly AM, Kontes F. Nat. Prod. Rep. 2011; 28: 897
- 2c Synder SA. Recent Adv. Polyphenol Res. 2012; 3: 311
- 2d Li WL, Zang P, Li HF, Yang SX. Prog. Chem. 2012; 24: 545
- 2e Li WL, Lv T, Yang YH, Yang YD. Chin. J. Chem. 2013; 33: 2443
- 2f Keylor MH, Matsurra BS, Stephenson CR. J. Chem. Rev. 2015; 115: 8976
- 3a Li X.-M, Huang K.-S, Lin M, Zhou L.-X. Tetrahedron 2003; 59: 4405
- 3b Yao C.-S, Lin M. Heterocycles 2006; 68: 983
- 4a Zhou LX, Lin M. Chin. Chem. Lett. 2000; 11: 515
- 4b Zhou LX, Lin M. Acta Pharm. Sin. 2000; 35: 669
- 4c Yao CS, Zhou LX, Lin M. Chem. Pharm. Bull. 2004; 52: 238
- 4d Li WL, He KK, Li Y, Hou ZJ. Acta Chim. Sin. 2005; 63: 1607
- 4e Wang X.-F, Zhang Y, Lin M.-B, Yao C.-S, Shi J.-G. J. Asian Nat. Prod. Res. 2014; 16: 511
- 5a Li WL, Luo YL, Li HF, Zang P, Han XQ. Synthesis 2010; 3822
- 5b Li WL, Yang SX, Lv T, Yang YD. Org. Biomol. Chem. 2014; 12: 2273
For reviews, see: