A spiroisoxazolinoproline-based amino acid scaffold for solid phase and one-bead - One-compound library synthesis

Seth M. Dixon; Kristin A. Milinkevich; Jeffrey Fujii; Ruiwu Liu; Nianhuan Yao; Kit Lam; Mark J. Kurth

doi:10.1021/cc060090p

A spiroisoxazolinoproline-based amino acid scaffold for solid phase and one-bead - One-compound library synthesis

Seth M. Dixon, Kristin A. Milinkevich, Jeffrey Fujii, Ruiwu Liu, Nianhuan Yao, Kit Lam, Mark J. Kurth

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

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 of this spiroisoxazolinoproline-based amino acid scaffold was performed during the synthesis of a sample library with high yields and high purity that validated the efficiency of the chemistry that was employed in resin-bound library synthesis. A 129 600 member one-bead - one-compound (OBOC) library based on the scaffold 7 was synthesized utilizing a dual amino acid encoding method and bifunctionalization of TentaGel resin.

Original language	English (US)
Pages (from-to)	143-157
Number of pages	15
Journal	Journal of Combinatorial Chemistry
Volume	9
Issue number	1
DOIs	https://doi.org/10.1021/cc060090p
State	Published - Jan 2007

ASJC Scopus subject areas

Drug Discovery
Organic Chemistry
Chemistry(all)
Discrete Mathematics and Combinatorics

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abstract = "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 of this spiroisoxazolinoproline-based amino acid scaffold was performed during the synthesis of a sample library with high yields and high purity that validated the efficiency of the chemistry that was employed in resin-bound library synthesis. A 129 600 member one-bead - one-compound (OBOC) library based on the scaffold 7 was synthesized utilizing a dual amino acid encoding method and bifunctionalization of TentaGel resin.",

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AU - Liu, Ruiwu

AU - Yao, Nianhuan

AU - Lam, Kit

AU - Kurth, Mark J.

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A spiroisoxazolinoproline-based amino acid scaffold for solid phase and one-bead - One-compound library synthesis

Abstract

ASJC Scopus subject areas

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