Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis |
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Authors: | Chojnacka Kinga Santoro Stefano Awartani Radi Richards Nigel G J Himo Fahmi Aponick Aaron |
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Institution: | Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611, USA. |
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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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