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ISBN 9783843915960

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978-3-8439-1596-0, Reihe Organische Chemie

Hai Vu Nghiem
Total Synthesis of Azachlorins and Azacorrins and a Concise Synthesis of a Naturally Occurring Isobacteriochlorin

222 Seiten, Dissertation Universität Bremen (2014), Softcover, A5

Zusammenfassung / Abstract

First part: Azachlorins 7, 11 and azahexadehydrocorrin rac-10 are novel structural types of tetrapyrrolic macrocycles. Synthesis of the target structures bearing nitrogen atoms in the beta-periphery of the macrotetracycles could be achieved by attaching an imidazole moiety 4 to the tricyclic nickel complex rac-5 followed by cyclization. Depending on the central metal ion of the bilin intermediates rac-6a,b chlorin or corrin type structures were formed on cyclization.

Second part: 12,18-didecarboxysirohydrochlorin is partially synthesized in an efficient six-step synthesis from hematoporphyrin. Compared to approaches so far reported by Battersby which comprehend more than twenty synthetic steps to furnish heme d1 and siroheme it is obvious that the here elaborated strategy is much superior. Another advantage consists in the possibility to adopt the strategy for synthesis of enantiomerically pure sirohydrochlorin type structures. Bioenzymatic studies with the product mixture of diasteromers should allow further investigations of biosynthesis of heme d1.