Synthesis of vinca alkaloids and related compounds. Part XCIII. Skeletal rearrangement of cyclovinblastine derivatives: Formation of a novel bisindole system

Bisindole alkaloids of the vinblastine (VLB) type can be oxidized to give a Psi-aspidosperma-aspidosperma type skeleton via 3'-7'-transannular cyclization. Acid catalysis triggers an aspidospermane-->eburnane skeletal rearrangement of these cyclic derivatives, thus giving a novel bisind...

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Bibliographic Details
Published inHeterocycles Vol. 50; no. 1; pp. 169 - 194
Main Authors Honty, K, Demeter, A, Szantay, C, Hollosi, M, Kolonits, P
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HIDDEN EXCHANGE PARTNER
BIS-INDOLES
INDOLE ALKALOIDS
NOE ANALYSIS
VINBLASTINE-TYPE
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Summary:Bisindole alkaloids of the vinblastine (VLB) type can be oxidized to give a Psi-aspidosperma-aspidosperma type skeleton via 3'-7'-transannular cyclization. Acid catalysis triggers an aspidospermane-->eburnane skeletal rearrangement of these cyclic derivatives, thus giving a novel bisindole system with a Psi-eburnea-aspidosperma type skeleton. A previously unexplored aspect of this transformation is the observed retention or inversion at C(16') depending on the starting C(16') configuration. The present paper gives a detailed account of the synthetic aspect of this work together with preliminary NMR and CD results concerning the epimerization at C(16').
ISSN:0385-5414
DOI:10.3987/com-98-s(h)25