A Spiroisoxazolinoproline-Based Amino Acid Scaffold for Solid Phase and One-Bead-One-Compound Library Synthesis

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• 作者：Seth M. Dixon ; Kristin A. Milinkevich ; Jeffrey Fujii ; Ruiwu Liu ; Nianhuan Yao ; Kit S. Lam ; Mark J. Kurth
• 刊名：Journal of Combinatorial Chemistry
• 出版年：2007
• 出版时间：January 2007
• 年：2007
• 卷：9
• 期：1
• 页码：143 - 157
• 全文大小：294K
• 年卷期：v.9,no.1(January 2007)
• ISSN：1520-4774

文摘

An efficient, multigram synthesis of a spiroisoxazolinoproline-based amino acid, 7, requiring minimal purification, delivering good cis:trans diastereoselectivity (~1:4), and providing good yields is reported. Surface-bound studies of the reduction of an arylnitro group in the presence of an isoxazoline ring with tin(II)dichloride dihydrate were undertaken to confirm the stability of the isoxazoline ring. Full derivitization ofthis spiroisoxazolinoproline-based amino acid scaffold was performed during the synthesis of a samplelibrary with high yields and high purity that validated the efficiency of the chemistry that was employed inresin-bound library synthesis. A 129 600 member one-bead-one-compound (OBOC) library based on thescaffold 7 was synthesized utilizing a dual amino acid encoding method and bifunctionalization of TentaGelresin.