120296-30-2Relevant articles and documents
Total synthesis of (-)-eudistomins with an oxathiazepine ring. Part 1. Formation of the oxathiazepine ring system
Nakagawa, Masako,Liu, Jin-Jun,Hino, Tohru,Tsuruoka, Akihiko,Harada, Naoyuki,Ariga, Makoto,Asada, Yasunori
, p. 3477 - 3486 (2007/10/03)
Formation of the oxathiazepine ring in eudistomins 1 was investigated. Thiazolidinyl-β-carboline 5 was successfully transformed into thiaindoloquinolizidine 7, but attempted oxidative transformation of 7 to 1 was not successful. The oxidative cyclization of 1-substituted-2 hydroxy-β-carboline 24 with NCS or the acid-catalyzed cyclization of the corresponding 5-oxide 26 with TsOH gave oxathiazepine 25, which was readily converted to (+)-debromoeudistomin L (+)-lf. (-)-Debromoeudistomin L (-)-lf was prepared from N-hydroxytryptamine 11 and the D-cysteinal 30. The Royal Society of Chemistry 2000.