Naturalproductman’s Blog

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Synthesis of Deoxystrigol

Posted by naturalproductman on April 13, 2009

Minoru Ueda and Mitsuru Shoji from Tohoku University has published recently in JOC on the synthesis of this polycyclic ring system.  Any ideas on how they coupled the aldehyde with an alpha,beta-unsaturated ester to make that lacone ring system?  This molecule is secreted by a fungus in the roots of a plant that signals the branching of the fungus.  This molecule is a strigolactone, which has the 6,5,5-lactone ring system and it is derived from a carotenoid.

lactone system

JOC paper


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