Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis.

Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611, USA.
Organic & Biomolecular Chemistry (Impact Factor: 3.49). 06/2011; 9(15):5350-3. DOI: 10.1039/c1ob05751k
Source: PubMed

ABSTRACT We report a new method for constructing the ABC ring system of strigolactones, in a single step from a simple linear precursor by acid-catalyzed double cyclization. The reaction proceeds with a high degree of stereochemical control, which can be qualitatively rationalized using DFT calculations. Our concise synthetic approach offers a new model for thinking about the (as yet) unknown chemistry that is employed in the biosynthetic pathways leading to this class of plant hormones.

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May 19, 2014