Biosynthesis. Part 30.1 Colchicine: studies on the ring expansion step focusing on the fate of the hydrogens at C-4 of autumnaline

Autor:	Amanda J. Murtagh, Alan C. Barker, Robert N. Woodhouse, Richard B. Herbert, Keith E. Suckling, Alan R. Battersby, James Staunton, Peter W. Sheldrake
Rok vydání:	1998
Předmět:	chemistry.chemical_compound medicine.anatomical_structure Carbon atom chemistry Biosynthesis Stereochemistry medicine Colchicine Ring (chemistry) Tropolone Nucleus
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :3003-3010
ISSN:	1364-5463 0300-922X
Popis:	The dienone ring of the intermediate 2 undergoes expansion to form the tropolone nucleus as N-formyldemecolcine 3 and colchicine 4 are biosynthesised. The additional carbon atom needed to form the 7-membered ring is provided by C-12 of the dienone 2 whilst C-13 becomes the N-formyl group of 3. It is shown by incorporation experiments using Colchicum plants with precursors (as 1) stereospecifically 3H-labelled at the centre corresponding to C-13 of 2 that HS is entirely lost whereas HR is fully retained as N-formyldemecolcine 3 is formed. The syntheses of the labelled precursors (as 1) are described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8092e75d583faf63d38f0f41aa7aca28 https://doi.org/10.1039/a803853h Zobrazit plný text záznamu