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

L. J. Bromhead; A. R. Norman; K. C. Snowden; B. J. Janssen; C. S. P. McErlean

doi:10.1039/C8OB01287C

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

L. J. Bromhead,‡^a A. R. Norman,‡^a K. C. Snowden,

^b B. J. Janssen

^b and C. S. P. McErlean

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry, The University of Sydney, NSW, Australia
E-mail: christopher.mcerlean@sydney.edu.au
Fax: +61 2 9351 3329
Tel: +61 2 9351 3970

^b The New Zealand Institute for Plant & Food Research Limited, Private Bag 92169, Auckland, New Zealand

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.

This article is part of the themed collection: Total synthesis in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB01287C
Article type: Paper
Submitted: 31 May 2018
Accepted: 11 Jul 2018
First published: 12 Jul 2018

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Org. Biomol. Chem., 2018,16, 5500-5507

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

L. J. Bromhead, A. R. Norman, K. C. Snowden, B. J. Janssen and C. S. P. McErlean, Org. Biomol. Chem., 2018, 16, 5500 DOI: 10.1039/C8OB01287C

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Organic & Biomolecular Chemistry

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

Abstract

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

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