ALKALOID SYNTHESIS VIA NITRONE CYCLOADDITIONS

通过硝酮环加成物合成生物碱

• 批准号: 3291844
• 负责人: PHILIP Ridley DESHONG
• 金额: $ 7.08万
• 依托单位: UNIV OF MARYLAND, COLLEGE PARK
• 依托单位国家: 美国
• 财政年份: 1986
• 资助国家: 美国
• 起止时间: 1986-07-01 至 1990-06-30
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3291844
• 关键词: anthracyclines; antineoplastic antibiotics; drug design /synthesis /production; drug screening /evaluation; kainate; neurotoxins; nitrone; pyrrolidines; silanes

The specific aim of the research outlined in this proposal is to synthesize the antitumor antibiotic menogarol (A). The strategy is divided into three parts: (1) the preparation of benzoxocin B which comprises the DEF-rings of menogarol, (2) the annulation of the anthracycline rings onto B, and (3) the manipulation of the functionality in the A ring to give menogarol. The proposal also includes a section concerning the use of 4- and 5-silyl-substituted isoxazolidines for the synthesis of allylic amines and the pyrrolidine neurotoxins kainic acid (C) and allo-kainic acid (D). Silylisoxazolidines are prepared by the [3+2] dipolar cycloaddition of nitrones and vinylsilanes.

本建议中概述的研究的具体目标是综合 抗肿瘤抗生素Menogarol（A）。 该战略分为三个 部分：（1）苯并氧杂环辛B的制备， menogarol，（2）蒽环类环在B上的成环，和（3） 操纵A环中的官能度以得到menogarol。 该提案还包括一个关于使用4-和 用于合成烯丙基胺的5-甲硅烷基取代的异恶唑烷， 吡咯烷神经毒素红藻氨酸（C）和别红藻氨酸（D）。 甲硅烷基异恶唑烷是通过[3+2]偶极环加成反应制备的， 硝酮和乙烯基硅烷。