Issue 15, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Kinga Chojnacka,a   Stefano Santoro,b   Radi Awartani,c   Nigel G. J. Richards,a   Fahmi Himob  and  Aaron Aponick*a  

* Corresponding authors

a Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611, USA
E-mail: aponick@chem.ufl.edu
Fax: +1-352-846-0296
Tel: +1-352-392-3484

b Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden
E-mail: himo@organ.su.se
Fax: +46-8-154908
Tel: +46-8-162476

c Petra Research, Inc., 12775 Rachael Boulevard, Alachua, FL 32615, USA
E-mail: petra@petraresearch.com
Fax: +1-386-462-0602
Tel: +1-386-462-0414

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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Article information

DOI
https://doi.org/10.1039/C1OB05751K
Article type
Communication
Submitted
12 May 2011
Accepted
07 Jun 2011
First published
08 Jun 2011

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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