New methods and reagents in organic synthesis. 92. A stereoselective synthesis of tilivalline and its analogs

S Mori, T Ohno, H Harada, T Aoyama, T Shioiri

Index: Mori, Shigehiro; Ohno, Tomoyasu; Harada, Hiroshi; Aoyama, Toyohiko; Shioiri, Takayuki Tetrahedron, 1991 ,  vol. 47,  # 27  p. 5051 - 5070

Full Text: HTML

Citation Number: 52

Abstract

Tilivalline (1a), a metabolite from Klebsiella pneumoniae var. oxytoca, and its derivatives 1 have been efficiently and stereoselectively synthesized from diphenyl phosphorazidate, the 2-oxazoline 2, the L-proline derivatives 5, and indole; the key step is a Mannich type intramolecular cyclization accompanied with completely stereoselective introduction of indole. Furthermore, 11-substituted 5H-pyrrolo [2, 1-c][1, 4] benzodiazepin-5-ones (16) ...