光辅助获取对映纯构象锁定的核糖呋喃胺与噁唑烷二酮哌嗪螺环连接。
Photoassisted access to enantiopure conformationally locked ribofuranosylamines spiro-linked to oxazolidino-diketopiperazines.
机构信息
Department of Chemistry and Biochemistry, University of Denver , Denver, Colorado 80208, United States.
出版信息
ACS Comb Sci. 2013 Jan 14;15(1):73-6. doi: 10.1021/co3001296. Epub 2012 Dec 4.
Abstract
N-Furoylated L-threonine-, serine-, or cysteine-based aminoacetals are coupled with o-aminoketones or aldehydes to offer rapid access to diverse enantiopure polyheterocycles possessing conformationally locked aminoglycoside-containing molecular scaffolds. The key step involves photogeneration of azaxylylenes which undergo [4 + 4] or [4 + 2] cycloadditions to the tethered furoyl pendants.
摘要
N-呋喃酰基-L-苏氨酸、丝氨酸或半胱氨酸基缩醛与邻氨基酮或醛缩合，可快速得到具有构象固定的含氨基糖苷分子支架的各种对映纯多杂环。关键步骤涉及氮杂环丁二烯的光生成，该氮杂环丁二烯与连接的呋喃酰基侧链发生[4+4]或[4+2]环加成反应。
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