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Published on: March 9, 2018
Total Synthesis and Stereochemical Confirmation of Heliolactone
Stone Woo1, Christopher S P McErlean1
1School of Chemistry , University of Sydney , Sydney , NSW 2006 , Australia.
Abstract:
Until now, the relative stereochemistry of the noncanonical strigolactone, heliolactone, has remained ambiguous. The total synthesis of heliolactone is described, with the key bond-forming event being a Stille cross-coupling that relied upon a reversal of the nucleophile-electrophile coupling partners. Spectroscopic analysis of synthetic heliolactone (and other stereoisomers) and comparisons with the isolated material enabled the absolute and relative stereochemistry of heliolactone to be secured.
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