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Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis†
Kinga Chojnacka,Stefano Santoro,Radi Awartani,Nigel G. J. Richards,Fahmi Himo,Aaron Aponick
Organic & Biomolecular Chemistry Pub Date : 06/08/2011 00:00:00 , DOI:10.1039/C1OB05751K
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.

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