Abstract
Two new methods for the introduction of a carbon side chain at the C3-position of indoles are presented. The first one is the palladium-catalyzed allylation of 3-bromoindoles with various allyl esters in the presence of hexa-n-butylditin. This is a new type of cross-coupling reaction which does not involve an organometallic reagent as a coupling partner. The second one is the vinylation of bromoindole in the presence of stoichiometric amount of Pd (II) salt. The reaction occurs selectively at the C3-position without affecting the carbon-bromine bond. The first total synthesis of optically acive clavicipitic acid is accomplished by a biomimetic route starting from 4-bromodehydrotryptophan which was prepared in one-step from 4-bromoindole by applying the above selective vinylation.
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