Tetrahedron p. 5051 - 5070 (1991)
Update date:2022-08-03
Topics:
Mori, Shigehiro
Ohno, Tomoyasu
Harada, Hiroshi
Aoyama, Toyohiko
Shioiri, Takayuki
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) have been also synthesized from the acetal amide 9a and various nucleophiles by the use of this new Mannich type cyclization.
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