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Synthesis of fercoprolone, a degraded prenylated coumarin

✍ Scribed by Giovanni Appendino; Giancarlo Cravotto; Giovanni Palmisano; Rita Annunziata

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 571 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00621-8

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✦ Synopsis

The degraded prenylated counmrin fercoprolone (la) was prepared from 4-hydroxycoumarin in five sleps and overall 13% yield. Key sleps were the oxidalive addition of 4-hydroxycoumarin to an alkene and the Barbier-typ¢ allylation era ketone carbonyl. Natural fercoprolone is racemic. The relative stcreochemistry of the glycol moiety was tenlatively assigned on the basis of mechanislic consideralions, further backed up by the stcreospecific and biomimetic synthesis of model compounds.

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