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Org Biomol Chem. 2009 Sep 7;7(17):3413-20. doi: 10.1039/b907026e. Epub 2009 Jul 2.

A new class of conjugated strigolactone analogues with fluorescent properties: synthesis and biological activity.

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  • 1Department of Agronomy and Natural Resources Inst. of Plant Sciences ARO, the Volcani Center Bet Dagan, 50250, Israel.

Abstract

A new class of strigolactone analogues has been synthesized. They differ from known molecules, both of natural and synthetic origin, in two main features. The conjugated system extends from the enol ether bridge to the A ring, the B ring is a heterocycle while the C ring is a cyclic ketone instead of a gamma-lactone. The key step of the synthesis is a Nazarov cyclization on activated substrates. Bioassays using Orobanche seeds have revealed that all the molecules strongly stimulate germination; in particular the oxygen containing analogues are the most active. Interestingly, some of the new molecules show fluorescent properties.

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