Enantioselective total synthesis and biological evaluation of (-)-solanacol

Organic & Biomolecular Chemistry
Liam J BromheadChristopher S P McErlean

Abstract

An enantioselective synthesis of the phenyl ring-containing strioglactone, (-)-solanocol, is described. Application of a Dynamic Kinetic Resolution (DKR) in the stereo-defining step enabled a step-economical synthesis to be achieved, and allowed access to natural and non-natural enantiomers with equal facility. Results of seed germination assays and Differential Scanning Fluorimetry (DSF) measurements with the known strigolactone receptor protein, Decreased Apical Dominance 2 (DAD2), are reported.

References

Jul 21, 2001·The Journal of Organic Chemistry·M J White, F J Leeper
Aug 14, 2003·Chemical Reviews·Barry M Trost, Matthew L Crawley
Mar 19, 2008·The New Phytologist·Juan Antonio López-RáezHarro Bouwmeester
Aug 12, 2008·Nature·Mikihisa UmeharaShinjiro Yamaguchi
Feb 18, 2009·Pest Management Science·Koichi YoneyamaYasutomo Takeuchi
Feb 18, 2009·Pest Management Science·Binne ZwanenburgDivakaramenon Sethumadhavan
Mar 3, 2010·Journal of Experimental Botany·Hinanit KoltaiYoram Kapulnik
Apr 21, 2010·Plant & Cell Physiology·Koichi YoneyamaYasutomo Takeuchi
Aug 7, 2010·Annual Review of Phytopathology·Xiaonan XieKoichi Yoneyama
Nov 26, 2010·Chemistry : a European Journal·Victor X ChenJean-Marie Beau
Aug 9, 2011·Journal of Agricultural and Food Chemistry·Kotomi UenoYukihiro Sugimoto
Jun 27, 2012·The Journal of Organic Chemistry·Oldamur HollóczkiLászló Nyulászi
Dec 4, 2012·Molecular Plant·Binne Zwanenburg, Tomás Pospísil
Jan 8, 2013·Frontiers in Plant Science·Bart J Janssen, Kimberley C Snowden
Jan 16, 2014·The Journal of Organic Chemistry·Liam J BromheadChristopher S P McErlean
Mar 24, 2015·Bioscience, Biotechnology, and Biochemistry·Hiroshi KumagaiHirosato Takikawa
Dec 23, 2015·Organic & Biomolecular Chemistry·J C Morris, C S P McErlean
Apr 24, 2016·Planta·Gavin R FlemattiSteven M Smith
Aug 2, 2016·Nature·Ruifeng YaoDaoxin Xie

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Citations

Dec 14, 2018·Organic Letters·Bishnupada SatpathiS S V Ramasastry
Sep 3, 2021·Chemical & Pharmaceutical Bulletin·Yoshiji Takemoto

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Methods Mentioned

BETA
thermal shift
column chromatography

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