Synthesis of vinca alkaloids and related compounds. Part 109. An intramolecular [4+2] cycloaddition mediated biomimetic synthesis of (+/-)-iboxyphylline

The pentacyclic alkaloid 1 could be synthesized by an intramolecular [4+2] cycloaddition reaction of intermediate 11, which had been obtained from tryptamine derivative 4 and aldehyde 5. After full epimerization of 13 the cyclization reaction furnished a mixture of 14a and 14b. Separation of the ste...

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Published inHeterocycles Vol. 75; no. 1; pp. 65 - 76
Main Authors Toth, Florian, Kalaus, Gyoergy, Pipa, Gergely, Greiner, Istvan, Szollosy, Aron, Rill, Attila, Gomory, Agnes, Hazai, Laszlo, Szantay, Csaba
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
IBOXYPHYLLINE
ASPIDOSPERMANE
PATHWAY
BUILD
SKELETON
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Summary:The pentacyclic alkaloid 1 could be synthesized by an intramolecular [4+2] cycloaddition reaction of intermediate 11, which had been obtained from tryptamine derivative 4 and aldehyde 5. After full epimerization of 13 the cyclization reaction furnished a mixture of 14a and 14b. Separation of the stereoisomers 14a and 14b and subsequent reduction with LiAlH4 resulted in (+/-)-iboxyphylline (14a -> 1) and its epimer, (+/-)-20-epiiboxyphylline (14b -> 15).
ISSN:0385-5414
1881-0942
DOI:10.3987/com-07-11172