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Organische Chemie und Naturstoffe

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Bei Biosyntheseuntersuchungen muB deshalb auch den beteiligten RingschluBmechanismen (~79, 791,285, 286) eine zentrale Bedeutung einger~iumt werden. Im folgenden soll gezeigt werden, dab die Natur nicht nur aus wenigen Bausteinen (Aminos~iuren, Essigs~iure, Mevalons~ure, C1-K6rper und Ammoniak) sondern auch mit einer geringen Zahl immer wiederkehrender Reaktionstypen den gewaltigen Formenreichtum der heterocyclischen Verbindungen aufbaut. 2, Cyclisierungsmechanismen Im Zuge der Arbeiten zur Darstellung yon Alkaloiden unter ,,zellm6glichen" Bedingungen sch~ilten sich folgende charakteristische Reaktionstypen heraus: Aldehydammoniak-Bildung, Aldolkondensation und Mannich-Kondensation.

565). Dadurch ist die Kntipfung von C--C-, C-N- oder C-O-Bindungen m6glich, wobei der nucleophile Substituent in ortho538 Cyclisierungsmechanismen bci der Alkaloid-Biosynthese oder para-Stellung zum phenolischen Hydroxyl angreifen kann. B. flit die Isochinolinalkaloide typisch ist (s. 5). B. beim oxydativen Abbau des Tryptophans zu Kynurenin (218) oder yon 3-Hydroxyanthranilsiture zu ~-Amino-f~-carboxymucons/iuresemialdehyd (s. S. 550). Heterocyclische Ringe lassen sich zwischen C-C, C-N und C-O aufbrechen.

J. Holland: The N a t u r e of Sulfur Bonding in m, [3-Unsaturated Sulfides and Sulfonium Salts. J. Am. Chem. Soc. 88, 5747 (1966). 12. , R. C. Corley, and M . E. Wall: Steroids L X X V I (I). Stereospecific Formation of ce- and ~-Epoxides in the Reaction of Dimethylsulfonium Methylide and Dimethylsulfoxonium Methylide with Dihydrotestosterone. Tetrahedron Letters (London) 14, 891 (1965). 13. Corey, E. , and M . Chaykovsky: Dimethyloxosulfonium Methylide and Dimethylsulfonium Methylide. F o r m a t i o n a n d Application to Organic Synthesis.

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