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- W2106605937 abstract "2,3-Dehydroprolyl-prolinanhydrid (6) und 2,3-Dehydroprolyl-2,3-dehydroprolinanhydrid (2) werden durch Eliminierung von Methylmercaptan aus cis-3-(Methylmercapto)prolyl-prolinanhydrid (5a) und cis- oder trans-3,6-Bis(methylmercapto)prolyl-prolinanhydrid (1a, 1b) hergestellt. Oxidation der Thioäther (5a, 1a, 1b) liefert die entsprechenden Sulfone (10a) bzw. Hydroperoxide (12a, 14b). Letztere werden zu den Hydroxiden (13a, 15b) reduziert. Sulfone und Hydroxide sind nucleophilen Substitutionsreaktionen durch Schwefelfunktionen zugänglich. Auf diese Weise ist es möglich, das Isomerengemisch 1a + 1b in racemisches Epidisulfid 20 umzuwandeln. Die Stereochemie dieser nucleophilen Reaktionen wird untersucht: Bei nucleophilen Reaktionen an nur einem der asymmetrischen Kohlenstoffatome des cis-Prolyl-prolinanhydrids bleibt die Konfiguration erhalten, bei Reaktionen an beiden asymmetrischen Kohlenstoffatomen wird das thermodynamisch stabilere Isomere (ld oder ll + dd) gebildet. On Amino Acids and Peptides, VI. Studies in the Synthesis of the Antibiotics Gliotoxin, Sporidesmin, Aranotin, Chaetocin, and Verticillin, VI. Nucleophilic Introduction of Sulfur Functions via Sulfones and Hydroxy Derivatives of Cyclic Dipeptides (Dioxopiperazines) 2,3-Dehydroprolyl-proline anhydride (6) and 2,3-dehydroprolyl-2–3-dehydroproline anhydride (2) are prepared by elimination of methanethiol from cis-3-(methylthio)prolyl-proline anhydride (5a) and cis- or trans-3,6-bis(methylthio)prolyl-proline anhydride (1a, 1b). Oxidation of the sulfides (5a, 1a, 1b) affords the corresponding sulfones (10a) and hydroperoxides (12a, 14b). 12a and 14b are reduced to the hydroxides 13a and 15b. Sulfones and hydroxides undergo nucleophilic displacement reactions with sulfur functions. In this way it is possible to convert the mixture of the isomeric sulfides 1a and 1b to racemic epidithioprolyl-proline anhydride (20). The steric course of these nucleophilic reactions is examined. Retention of configuration is observed in displacement reactions involving only one asymmetric carbon of cis-prolyl-proline anhydride. Reactions involving both asymmetric carbons yield the thermodynamically more stable isomer (ld or ll + dd)." @default.
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- W2106605937 date "1973-01-01" @default.
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- W2106605937 title "Über Aminosäuren und Peptide, VI. Syntheseversuche in der Reihe der 3,6‐Epidithio‐2,5‐dioxopiperazin‐Antibiotika Gliotoxin, Sporidesmin, Aranotin, Chaetocin und Verticillin, VI. Nucleophile Einführung von Schwefelfunktionen über Sulfone und Hydroxyderivate cyclischer Dipeptide (Dioxopiperazine)" @default.
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- W2106605937 doi "https://doi.org/10.1002/cber.19731060120" @default.
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