Abstract
l-Tryptophan immobilized on polystyrene−Wang resin was sequentially reacted with an aldehyde and Fmoc-amino acid chloride. This generates a transient N-acyliminium species which undergoes Pictet−Spengler condensation to give a mixture of cis and trans tetrahydro-β-carbolines. Removal of the Fmoc protecting group, with concomitant diketopiperazine formation, results in cyclative cleavage of the desired products from the resin.
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