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Abstract
A total synthesis of amauromine ( 1 ) is described. Starting with L-tryptophan, diketopiperazine 4 was synthesized in nine steps. Thio-Claisen rearrangement of the sulphonium cation derived from the key intermediate 4 proceeded at the two sites simultaneously to provide 3 along with 12 . Reductive desulphurization on 3 using TiCl 4-LiAlH 4 (1:2) resulted in concurrent cyclization to lead to amauromine ( 1 ).
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