Products of ozonolysis of L-1,4-cyclohexadienylalanine. Intramolecular cyclization and cyclization with hydroxylamine. The synthesis of two isomers of L-isoxazolylalanine.

Gury Zvilichovsky*, Vadim Gurvich

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Protected L-phenylalanine was reduced to L-1,4-cyclohexadienylalanine followed by ozonolysis of the unsaturated ring. Intramolecular cyclization of the ozonolysis product occurred upon treatment with acid. The cyclization of the product of ozonolysis with hydroxylamine was studied as well. The formation of both 5- and 3-isoxazolylalanine is demonstrated. Mechanism of formation of these products and structure of intermediates are discussed.

Original languageEnglish
Pages (from-to)4457-4468
Number of pages12
JournalTetrahedron
Volume53
Issue number12
DOIs
StatePublished - 24 Mar 1997

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