Enantioselective Total Synthesis of Communesin F

Communesin F 的对映选择性全合成

• 批准号: 8458641
• 负责人: Stephen Lathrop
• 金额: $ 4.48万
• 依托单位: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
• 依托单位国家: 美国
• 财政年份: 2012
• 资助国家: 美国
• 起止时间: 2012-04-01 至 2014-01-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/8458641
• 关键词: Academia; Alkaloids; Amines; Biological; Biological Factors; Biomimetics; Cancer cell line; Complex; DNA Sequence Rearrangement; Disease; Family; Genetic Recombination; Goals; Heterodimerization; Industry; Methods; Protocols documentation; Research Proposals; Route; Testing; United States National Institutes of Health; Work; diazene; dimer; insight; interest; member

DESCRIPTION (provided by applicant): The proposed work would enable the convergent, enantioselective, and biomimetic synthesis of the alkaloid natural product (-)-communesin F. (-)-Communesin F belongs to a family of natural products containing a structurally unique heptacyclic framework. This family of natural products displays a range of interesting biological activities. A biosynthetically inspired rearrangement of a complex heterodimer should afford the core of the communesin alkaloids. Application of our newly developed method for heterodimerization will allow rapid access to the necessary dimer. The method centers on the stepwise union of complex amines in the form of unsymmetrical diazenes followed by photoexpulsion of dinitrogen to afford the heterodimerized product. In all, the proposed route will afford a rapid and convergent synthesis of (-)- communesin F which potentially could be expanded to all members of the communesin family of natural products.

描述（由申请人提供）：所提出的工作将使生物碱天然产物（-）-communesin F的收敛，对映选择性和仿生合成成为可能。（-）-Communesin F属于含有结构独特的七环框架的天然产物家族。这个天然产物家族显示出一系列有趣的生物活性。一个复杂的异二聚体的生物合成启发重排应该提供的核心communesin生物碱。应用我们新开发的异源二聚化方法将允许快速获得必要的二聚体。该方法的核心是以不对称二氮烯的形式逐步结合络合胺，然后光排出二氮，得到异二聚产物。总而言之，拟议的路线将 提供了（-）- communesin F的快速和收敛合成，其潜在地可以扩展到天然产物的communesin家族的所有成员。