Sequential 1,3-dipolar cycloadditions in the synthesis of bis-isoxazolo substituted piperidinones

Kevin Sheng Lin Huang, Edwin H. Lee, Marilyn M. Olmstead, Mark J. Kurth

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

A strategy for the efficient synthesis of novel bis-isoxazolo substituted piperidinones has been developed. The protocol consists of the Michael addition of an unsaturated alkoxide to β-nitrostyrene followed by an intramolecular nitrile oxide cycloaddition (INOC) or an intramolecular silyl nitronate olefin cycloaddition (ISOC) to give III. Grignard addition to this isoxazoline intermediate followed by DCC coupling of the resulting isoxazolidine with nitroacetic acid gave II, and a second intramolecular cycloaddition via 1,3-dipoles result in the formation of the targeted novel tetracycles (I). A solid-supported scavenger was employed to increase the efficiency and yield of the Michael addition step.

Original languageEnglish (US)
Pages (from-to)499-503
Number of pages5
JournalJournal of Organic Chemistry
Volume65
Issue number2
DOIs
StatePublished - Jan 28 2000

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Cycloaddition
Nitriles
Alkenes
Oxides

ASJC Scopus subject areas

  • Organic Chemistry

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Sequential 1,3-dipolar cycloadditions in the synthesis of bis-isoxazolo substituted piperidinones. / Huang, Kevin Sheng Lin; Lee, Edwin H.; Olmstead, Marilyn M.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 65, No. 2, 28.01.2000, p. 499-503.

Research output: Contribution to journalArticle

Huang, Kevin Sheng Lin ; Lee, Edwin H. ; Olmstead, Marilyn M. ; Kurth, Mark J. / Sequential 1,3-dipolar cycloadditions in the synthesis of bis-isoxazolo substituted piperidinones. In: Journal of Organic Chemistry. 2000 ; Vol. 65, No. 2. pp. 499-503.
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