Synthesis of a B Ring Opened 7,8-seco-Vitamin B12 Derivative with Grob Fragmentation

Synthesis of a B Ring Opened 7,8-seco-Vitamin B12 Derivative with Grob Fragmentation

A synthetic route toward B ring opened 7,8-seco-cyanocobalamins is described. Hydrolysis of a novel c-lactone vitamin B12 (B12) derivative generates a cobalamin (Cbl) with a β-bromo alcoholate subunit that reacts in situ via Grob fragmentation to the secocorrin.

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Veröffentlicht in:Organic letters 2013-09, Vol.15 (18), p.4630-4633
Hauptverfasser: Oetterli, René M, Prieto, Lucas, Spingler, Bernhard, Zelder, Felix
Format: Artikel
Sprache:eng
Schlagworte:
Molecular Structure
Stereoisomerism
Vitamin B 12 - analogs & derivatives
Vitamin B 12 - chemical synthesis
Vitamin B 12 - chemistry
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Zusammenfassung:A synthetic route toward B ring opened 7,8-seco-cyanocobalamins is described. Hydrolysis of a novel c-lactone vitamin B12 (B12) derivative generates a cobalamin (Cbl) with a β-bromo alcoholate subunit that reacts in situ via Grob fragmentation to the secocorrin.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401572j