Total syntheses of (+/-)-cis- and trans-11-methoxydeethyleburnamonine

Authors
Ronkko, K Berner, M Jokela, R Tolvanen, A
Citation
K. Ronkko et al., Total syntheses of (+/-)-cis- and trans-11-methoxydeethyleburnamonine, J HETERO CH, 37(5), 2000, pp. 1145-1149
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
37
Issue
5
Year of publication
2000
Pages
1145 - 1149
Database
ISI
SICI code
0022-152X(200009/10)37:5<1145:TSO(AT>2.0.ZU;2-J
Abstract
The total syntheses of 11-methoxydeethyleburnamonines (4) and (13) were car ried out with use of 6-methoxytryptophyl bromide (5) as starting material. Compound 5 was converted in three steps to trans-ester 8. Acid-catalysed ep imerization of 8, lithium aluminum hydride reduction of the ester group, to sylation and substitution with cyanide gave the cis-nitrile 12. Acid-induce d cyclization of 12 yielded mainly (+/-)-tran-11-methoxydeethyleburnamonine (13), whereas base-induced cyclization gave (+/-)-cis-11-methoxydeethylebu rnamonine (4).