S. Takase, Y. Itoh, I. Uchida
1985
Citations
0
Influential Citations
21
Citations
Journal
Tetrahedron Letters
Abstract
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 ).