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Inorganic Cyanide as Protecting Group in the Stereospecific Reconstitution of Vitamin B12 from an Artificial Green Secocorrinoid

Prieto, Lucas and Neuburger, Markus and Spingler, Bernhard and Zelder, Felix. (2016) Inorganic Cyanide as Protecting Group in the Stereospecific Reconstitution of Vitamin B12 from an Artificial Green Secocorrinoid. Organic Letters, 18 (20). pp. 5292-5295.

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Official URL: http://edoc.unibas.ch/53916/

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Abstract

The synthesis of vitamin B 12 in four steps from an artificial green secocorrinoid is presented. The stereospecific reconstitution of the B-ring of the cobalamin involves a quantitative and rapid ligand-centered radical ring closure reaction leading first to a new B 12 derivative with antivitamin activity that is subsequently converted to the natural product. Chemoselectivity in the one-electron reduction of the macrocycle was achieved by introducing inorganic cyanide as an axially coordinating protecting group of the otherwise reduction-sensitive Co III -ion. The integrity of structure and function of the reconstituted natural product was unequivocally proven by single crystal structural analysis and a microbiological assay using Lactobacillus leichmannii .
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie
UniBasel Contributors:Neuburger, Markus
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:1523-7060
e-ISSN:1523-7052
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:01 Feb 2017 12:34
Deposited On:01 Feb 2017 12:34

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