Synlett 2002(10): 1691-1693
DOI: 10.1055/s-2002-34245
LETTER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of 2-Cyanomethyl-3-hydroxy-5-iodomethyltetrahydrofuran from Isoxazolines by Iodoetheration

Hyoung Cheul Kim, Seung Woo Woo, Min Jung Seo, Dong Ju Jeon, Zaesung No, Hyoung Rae Kim*
Medicinal Science Division, Korea Research Institute of Chemical Technology, P. O. Box 107, Yusong, Taejon 305-600, Korea
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Publication History

Received 31 July 2002
Publication Date:
23 September 2002 (online)

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Abstract

Diastereoselective 1,3-dipolar cycloaddition reaction of nitrile oxides with 1,5-hexadien-3-ol afforded syn-5-(1-hydroxy-3-butenyl)isoxazolines, which underwent iodoetheration by iodine monochloride to give 2-cyanomethyl-3-hydroxy-5-iodomethyl­tetrahydrofuran with diastereoselectivity. The relative stereo­chemistry of iodomethyl group varied depending on both the 3-substituents and the hydroxy protecting groups.