Details

Autor(en) / Beteiligte

• Preobrazhenskaya, M.N.
• Balashova, E.G.
• Turchin, K.F.
• Padeiskaya, E.N.
• Uvarova, N.V.
• Pershin, G.N.
• Suvorov, N.N.

Titel

Total synthesis of antibiotic indolmycin and its stereoisomers

Ist Teil von

• Tetrahedron, 1968-01, Vol.24 (19), p.6131-6143

Ort / Verlag

England: Elsevier Ltd

Erscheinungsjahr

1968

Link zum Volltext

Quelle

Elsevier Journal Backfiles on ScienceDirect (DFG Nationallizenzen)

Beschreibungen/Notizen

• The total synthesis of the antibiotic indolmycin [(−)-2-methylamino-5-α-(3′-indolyl)ethyl-2-oxazolin-4-one] and its stereoisomers via diastereoisomeric α-hydroxy-β-(3-indolyl)butyric esters has been described. Various 2,4-oxazolidinedione derivatives—analogues of indolmycin—were also obtained. The configuration of indolmycin was confirmed by the NMR spectra. Indolmycin in solution is a mixture of two conformers of an enaminoform with a restricted rotation around the CNHMe bond. The bacteriostatic and chemotherapeutic activity of (±)-indolmycin shows that he antibiotic is highly effective in vitro and in vivo against staphylococci producing penicillinase and staphyloccci which are polyresistant. (—)-Indolmycin in vitro is twice as active as its racemate.