Tetrahedron letters

New methods and reagents in organic synthesis. 65. A stereoselective synthesis of tilivalline

S Mori, T Aoyama, T Shioiri

Index: Mori, Shigehiro; Aoyama, Toyohiko; Shioiri, Takayuki Tetrahedron Letters, 1986 ,  vol. 27,  # 50  p. 6111 - 6114

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Citation Number: 17

Abstract

Abstract Tilivalline (1), a metabolite from Klebsiella, has been efficiently and stereoselectively synthesized from diphenyl phosphorazidate (DPPA), the 2-oxazoline 2, the L-proline derivative 5, and indole: the key step is a Mannich type intramolecular cyclization accompanied with simultaneous and completely stereoselective introduction of indole.