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Soc. 87, 3460 (1965). 90. Swain, C. , and E. R. Thornton : Mechanism of c~-Elimination b y Hydroxide Ion on p-Nitrobenzyl-sulfonium-Ion in Aqueous Solution. J. Am. Chem. Soc. 83, 4033 (1961). 91. , and T. S. Stevens: Degradation of Q u a r t e r n a r y A m m o n i u m Salts, P a r t V. Molecular R e a r r a n g e m e n t in Related Sulphur Compounds. J. Chem. Soc. (London) (7932) 69. 92. Trayndis, V. , and J. V. McSweeney : Ylide Methylation of Aromatic Nitro Compounds. J. Org. Chem. 31,243 (1966).

Chem. Soc. 84, 867 (1962). 17. --, a n d W. Oppolzer: Transfer of Alkyl-Substituted Methylenes from Sulfonium Alkylides to Carbonyl Groups. J. Am. Chem. Soc. 86, 1899 (1964). 18. --, and M . Chaykovsky: Concerning the Reaction of Sulfonium Methylides with conjugated Carbonyl Compounds. T e t r a h e d r o n Letters (London) 4, 169 (1963). 19. -- -- Dimethylsulfonium Methylide, a Reagent for selective Oxirane Synthesis from Aldehydes and Ketones. J. Am. Chem. Soc. 84, 3782 (1962). 20. - - -- F o r m a t i o n and Photochemical R e a r r a n g e m e n t of ~'-Kctosulfoxonium Ylides.

Die Biosynthese dieser cyclischen Iminos~iure wird durch die HO~ -~ COOH XlX Glutamins iiure ~COOH XXll AI -Pyrrolin5 -carbons~iure H2N~COOH '' ~ XVIH p~-~H z XX Ornithin Putrescin XXI ZXl -Pyrrolin- XXIII ,xl -Pyrrolin 2 -carbons ~ure H•COOH/ HO~CH20H x H~COOH XXIV Prolin (in Tieren u. N. crassa) XXVlI Retronecin XXIV Prolin (in Pflanzen) / , OR XXV Tropanalkaloide CHa CH3 XXVIII Cus khygrin XXVI Nicotin Schema 6. tsN] Reduktion der 7-Carboxylgruppe der Glutamins~ture eingeleitet. Dabei entsteht Glutamins~ture-y-semialdehyd, der spontan zu A1-Pyrrolin-5carbons~ure (XXI) cyclisieren kann.

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