ISSN:
0170-2041
Keywords:
Indoles
;
Alkaloids
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A Simple Entry into the Series of Tetracyclic Hetero- and Secoyohimbanes, Strychnos and Oxindole AlkaloidsThe divinylogous urethane 4a reacts in diluted acetic acid to give the indolochinolizine 9 (yield 40%). The total amount grows up to 65%, if compound 14, prepared from 4a in nearly quantitative yield, is allowed to react with trifluoroacetic acid for a few minutes. Similarily, 4b and 4c give by treatment with SnCl2 and heat in an [4+2]-cycloaddition reaction the spiroindolines 17 and 18. Oxytryptamine reacts with 2 moles of 2 to give immediately the spirooxindole 21. This compound can be rearranged to give 23 (after treatment with acid, reduction and catalytic hydrogenation). 23 has the cis-configuration of rhyncophylline.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940208
