CAREER: Synthesis of Zoanthamine Alkaloids by Cascade Reactions

职业：通过级联反应合成佐安他明生物碱

• 批准号: 1150606
• 负责人: Jiong Yang
• 金额: $ 47.5万
• 依托单位: Texas A&M University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2012
• 资助国家: 美国
• 起止时间: 2012-09-01 至 2014-08-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1150606&HistoricalAwards=false
• 关键词: CAREER; Synthesis; Zoanthamine; Alkaloids; Cascade

With this CAREER Award, the Chemical Synthesis program is supporting the research of Professor Jiong Yang of Texas A&M University. Professor Yang will develop efficient synthetic approaches to zoanthamines, a family of complex polycyclic marine alkaloids possessing biological properties that are valuable for therapeutic applications. First, a transannular Michael reaction cascade will be systematically explored to elucidate its scope and stereochemical outcome for synthesis of polycyclic molecular structures. Second, the total synthesis of norzoanthamine, an anti-osteoporotic member of natural products of the zoanthamine family, will be completed. The transannular Michael reaction cascade will be employed to synthesize its stereochemically complex and highly functionalized ABC ring system. Other cascade reactions will also be developed for efficient assembly of the complex polycyclic molecular skeleton of zoanthamines. For the final objective, a synthetic route to 28-deoxyzoanthenamine will be developed based on a proposed biosynthetic scheme.Professor Yang will also initiate educational projects that interweave research and teaching. The first project involves an outreach program targeting local high school science educators by providing opportunities for professional development through discovery-based research in his laboratory. The second initiative involves outreach to K-12 students through a Chemistry Laboratory Open House program to share the excitement of scientific research/discoveries and encourage these students to consider exploring STEM fields.

凭借这一职业奖，化学合成项目正在支持德克萨斯农工大学杨炯教授的研究。 杨教授将开发卓安胺的有效合成方法，卓安胺是一类复杂的多环海洋生物碱，具有对治疗应用有价值的生物特性。首先，将系统地探索跨环迈克尔反应级联，以阐明其合成多环分子结构的范围和立体化学结果。其次，将完成去甲安他明（安他明家族天然产物的抗骨质疏松成员）的全合成。跨环迈克尔反应级联将用于合成其立体化学复杂且高度功能化的ABC环系统。还将开发其他级联反应，以有效组装佐蒽胺复杂的多环分子骨架。为了实现最终目标，将根据拟议的生物合成方案开发28-脱氧苯胺胺的合成路线。杨教授还将启动研究和教学相结合的教育项目。 第一个项目涉及一项针对当地高中科学教育者的外展计划，通过实验室中基于发现的研究提供专业发展机会。第二项举措是通过化学实验室开放日计划向 K-12 学生进行推广，分享科学研究/发现的兴奋，并鼓励这些学生考虑探索 STEM 领域。