Unified approach to fused and spirocyclic oxindoles through lewis-acid-promoted opening of spiroepoxyoxindoles with allylsilanes: application to the formal synthesis of (+/-)-physovenine

TitleUnified approach to fused and spirocyclic oxindoles through lewis-acid-promoted opening of spiroepoxyoxindoles with allylsilanes: application to the formal synthesis of (+/-)-physovenine
Publication TypeJournal Article
Year of Publication2017
AuthorsSharma, BM, Yadav, M, Gonnade, RG, Kumar, P
JournalEuropean Journal of Organic Chemistry
Issue18
Pagination2603-2609
Date PublishedMAY
Type of ArticleArticle
ISSN1434-193X
Keywordsalkaloids, Allylation, annulation, Lewis acids, spiro compounds
Abstract

A protocol for the construction of oxindoles containing all-carbon quaternary centres in a highly regioselective manner has been developed. The reaction involves opening of spiroepoxyoxindoles with allylsilanes to give Hosomi-Sakurai-type products as well as new silicon-containing spirocyclic oxindoles. A formal synthesis of (+/-)-physovenine was accomplished in five steps using this protocol.
DOI10.1002/ejoc.201700259
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.882
Divison category: 
Physical and Materials Chemistry

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