A beta-lactone route to chiral gamma-substituted alpha-amino acids: application to the concise synthesis of (S)-alpha-azidobutyro lactone and a natural amino acid.
A beta-lactone route to chiral gamma-substituted alpha-amino acids: application to the concise synthesis of (S)-alpha-azidobutyro lactone and a natural amino acid.
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DOI：
10.1021/ol017120b
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发表时间：
2002-01
期刊：
影响因子：
5.2
通讯作者：
R. L. Tennyson;Guillermo S. Cortez;Hector J. Galicia;Charles R. Kreiman;C. Thompson;D. Romo
中科院分区：
文献类型：
--
作者：
R. L. Tennyson;Guillermo S. Cortez;Hector J. Galicia;Charles R. Kreiman;C. Thompson;D. Romo
[反应：见正文]β-内酯是有用的合成中间体，可以获得许多功能阵列。在这份报告中，对映体纯的4-三氯甲基-2-氧乙酮是一种多功能的氨基酸合成子，导致了各种伽马取代的α-氨基酸前体。这一方法的实用性通过从大银鱼种子中简明地合成受保护的高丝氨酸等效物-α-叠氮丁基内酯和自然产生的α-氨基酸来证明。
[reaction: see text] Beta-lactones are useful synthetic intermediates allowing access to a number of functional arrays. In this report, enantiomerically pure 4-trichloromethyl-2-oxetanone is shown to be a versatile amino acid synthon leading to a variety of gamma-substituted alpha-amino acid precursors. The utility of this methodology was demonstrated by the concise synthesis of a protected homoserine equivalent, alpha-azidobutyro lactone, and a naturally occurring alpha-amino acid from the seeds of Blighia unijugata.