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 language | English |
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Pages (from-to) | 4457-4468 |
Number of pages | 12 |
Journal | Tetrahedron |
Volume | 53 |
Issue number | 12 |
DOIs | |
State | Published - 24 Mar 1997 |