Abstract
The synthesis of side-chain 13C-labeled geranylgeranyl-4-hydroxybenzoic acids and geranylgeranyl-3,4-dihydroxybenzoic
acids is described. The synthesis starts from O-protected methyl hydroxyiodobenzoates, which are transformed into Grignard reagents
by low-temperature iodine-magnesium exchange according to Knochel’s procedure. Copper
catalyzed cross-coupling with labeled geranylgeranyl bromide followed by deprotection
affords the products with good yields and full retention of stereochemistry.
Key words
allylations - copper - coupling - Grignard reactions - organometallic reagents
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