Journal of Organic Chemistry p. 1166 - 1174 (1989)
Update date:2022-09-26
Topics:
Wenkert, Ernest
Guo, Ming
Pestchanker, Mauricio J.
Shi, Yao-Jun
Vankar, Yashwant D.
A series of indolo<2,3-a>quinolizidines have been prepared by the two-step scheme of nucleophile addition to 1-tryptophyl-3-acylpyridinium salts or their vinylogues and subsequent, acid-catalyzed cyclization.Acid-induced hydrolysis, decarboxylation, and reduction of the resultant vinylogous urethanes has opened an approach to antirhine and yielded C(15)-substituted deplancheine derivatives.Functional group manipulation of the latter has permitted the syntheses of geissoschizol and geissoschizine.
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