- New methods and reagents in organic synthesis. 92. A stereoselective synthesis of tilivalline and its analogs
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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.
- Mori, Shigehiro,Ohno, Tomoyasu,Harada, Hiroshi,Aoyama, Toyohiko,Shioiri, Takayuki
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p. 5051 - 5070
(2007/10/02)
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- NEW METHOD AND REAGENTS IN ORGANIC SYNTHESIS. 65. A STEREOSELECTIVE SYNTHESIS OF TILIVALLINE
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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.
- Mori, Shigehiro,Aoyama, Toyohiko,Shioiri, Takayuki
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p. 6111 - 6114
(2007/10/02)
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