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477-30-5

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Biosynthesis. Part 28.1,2 Colchicine: Definition of intermediates between O-methylandrocymbine and colchicine and studies on speciosine
Labelled samples are prepared of demecolcine 3, colchicine 4, N-formyl-N-deacetylcolchlcine 6 and N-deacetylcolchicine 7, the last depending on a new method for its preparation from colchicine. Incorporation experiments with these compounds and with specifically labelled autumnaline 1 support the pathway 2→5→3→6→7→4 as the terminal sequence for the biosynthesis of colchicine. The key intermediate O-methylandrocymbine 2 is isolated from Colchicum autumnale plants together with speciosine 14 and its O-acetyl derivative 15; all three are first isolations from this plant. Speciosine 14 and N-methyldemecolcine 8 are shown to be formed in vivo largely from demecolcine 3 whereas N-formyldemecolcine 5 is the precursor of demecolcine and its N-formyl group is derived from C-3 of autumnaline. This discovery of a tropolone alkaloid which retains both carbons of the ethanamine bridge of 2 is important for future stereochemical work on the ring-expansion process.
Barker, Alan C.,Julian, David R.,Ramage, Robert,Woodhouse, Robert N.,Hardy, Gilbert,McDonald, Edward,Battersby, Alan R.
p. 2989 - 2994
(2007/10/03)

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Chemical Properties

Melting Point: 73-75°C
Boiling Point: 625.5°Cat760mmHg
Flash Point:332.1°C
Density: 1.21g/cm³
Solubility:DMSO: 10 mg/mL
Storage Temp.:2-8°C
Vapor Pressure: 1.46E-15mmHg at 25°C
Refractive Index: 1.5614 (estimate)
PKA: 8.48±0.40(Predicted)
Sensitive: Air & Light Sensitive
BRN: 2822892
PSA: 66.02000
LogP: 3.34580

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