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Issue 15, 2011
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Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis

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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.

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

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Publication details

The article was received on 12 May 2011, accepted on 07 Jun 2011 and first published on 08 Jun 2011


Article type: Communication
DOI: 10.1039/C1OB05751K
Org. Biomol. Chem., 2011,9, 5350-5353

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

    K. Chojnacka, S. Santoro, R. Awartani, N. G. J. Richards, F. Himo and A. Aponick, Org. Biomol. Chem., 2011, 9, 5350
    DOI: 10.1039/C1OB05751K

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