Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides

Day, Jonathan; Uroos, Maliha; Castledine, Richard A.; Lewis, William; McKeever-Abbas, Ben; Dowden, James

Abstract

Cycloaddition reactions between pyridinium ylides and 3-alkenyl oxindoles that proceed in high yield and with very good regio- and diastereoselectivity are reported. The resulting cycloadducts have the same stereochemistry of biologically active oxindole alkaloids, such as strychnofoline.

Citation

Day, J., Uroos, M., Castledine, R. A., Lewis, W., McKeever-Abbas, B., & Dowden, J. (2013). Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides. Organic and Biomolecular Chemistry, 11(38), 6502-6509. https://doi.org/10.1039/c3ob41415a

• Journal Article Type: Article
• Acceptance Date: Aug 15, 2013
• Online Publication Date: Aug 15, 2013
• Publication Date: Aug 15, 2013
• Deposit Date: Apr 1, 2014
• Publicly Available Date: Apr 1, 2014
• Journal: Organic & Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 11
• Issue: 38
• Pages: 6502-6509
• DOI: https://doi.org/10.1039/c3ob41415a
• Public URL: https://nottingham-repository.worktribe.com/output/717062
• Publisher URL: http://pubs.rsc.org/en/content/articlelanding/2013/ob/c3ob41415a#!divAbstract