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

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 equ...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018, Vol.16 (30), p.5500-5507
Main Authors: Bromhead, L J, Norman, A R, Snowden, K C, Janssen, B J, McErlean, C S P
Format: Article
Language:English
Subjects:
Apical dominance
Enantiomers
Fluorimetry
Germination
Proteins
Seed germination
Synthesis
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01287c