Tetrahedron p. 5887 - 5894 (1986)
Update date:2022-09-26
Topics:
Takase, Shigehiro
Uchida, Itsuo
Tanaka, Hirokazu
Aoki, Hatsuo
Itoh, Yoshikuni
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 TiCl4-LiAlH4 (1:2) resulted in concurrent cyclization to lead to amauromine (1).
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Doi:10.1016/S0040-4039(00)87790-4
(1986)Doi:10.1007/BF00663850
(1987)Doi:10.1016/j.tetlet.2008.11.036
(2009)Doi:10.1016/j.tet.2008.11.036
(2009)Doi:10.1021/jo01103a032
(1958)Doi:10.1002/JLCR.1676
(2009)
