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Two Stereoisomeric Pentacyclic Oxindole Alkaloids From Uncaria Tomentosa: Uncarine C and Uncarine E

Two Stereoisomeric Pentacyclic Oxindole Alkaloids From Uncaria Tomentosa: Uncarine C and Uncarine E

I Muhammad, I A Khan, N H Fischer, F R Fronczek

Acta Crystallogr C. 2001 Apr;57(Pt 4):480-2.

PMID: 11313600

Abstract:

The chloroform solvate of uncarine C (pteropodine), (1'S,3R,4'aS,5'aS,10'aS)-1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxospiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid methyl ester, C(21)H(24)N(2)O(4).CHCl(3), has an absolute configuration with the spiro C atom in the R configuration. Its epimer at the spiro C atom, uncarine E (isopteropodine), (1'S,3S,4'aS,5'aS,10'aS)-1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxospiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid methyl ester, C(21)H(24)N(2)O(4), has Z' = 3, with no solvent. Both form intermolecular hydrogen bonds involving only the oxindole, with N.O distances in the range 2.759 (4)-2.894 (5) A.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP5171379-A	Uncarine E		5171-37-9	Price

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