CAREER: New Advances in the Cascade Rearrangement of Furylcarbinols for Complex Molecular Synthesis

有了这个职业奖，化学合成项目将支持加州大学圣巴巴拉分校的哈维尔·里德·德·阿拉尼兹教授的研究。里德·德·阿拉尼斯教授将应用新的策略来合成功能化的五元环。该方法将依赖于2-呋喃甲醇的多米诺骨牌重排，包括正式的4-pi电环化步骤，这提供了获得官能化环戊酮的有效途径，这些环戊酮本身对医学、生物学和材料科学都很重要。首先，将开发一种操作简单的合成方法来在一次操作中构建功能化的五元环以及氮杂环。分子内级联重排允许直接和高度非对映选择性地合成氮杂环天然产物核心。第二，将级联重排应用于四元立体中心的合成。在最终目标中，将努力实现对映性选择性的级联重组。哈维尔·里德·德·阿拉尼斯教授还将与加州大学圣巴巴拉分校的外联项目合作，帮助克服科学界少数族裔代表性不足的问题。里德·德·阿拉尼兹教授将担任加州大学卓越领导力至高级学位(UC Leads)项目的教师顾问。与加州大学LEADS项目合作，里德·德·阿拉尼兹教授将在夏季参与并领导一系列针对有前途的少数族裔本科生的专业发展研讨会。第二个教育倡议将为学生提供机会，在一个有组织但随意的午餐论坛上，与来自少数族裔/女性背景的博士后研究助理和教职员工互动。教师/博士后研究助理将讨论他们的职业道路，以及孤立和语言障碍、校园日益多样化、标签、同龄人误解和指导等主题。

With this CAREER Award, the Chemical Synthesis program is supporting the research of Professor Javier Read de Alaniz of the University of California-Santa Barbara. Professor Read de Alaniz will apply new strategies for the synthesis of functionalized five-membered rings. The approach will rely on a domino rearrangement of 2-furylcarbinols, involving a formal 4-pi electrocyclization step, that provides efficient access to functionalized cyclopentenones, themselves important to medicine, biology, and material science. First, an operationally simple synthetic methodology will be developed to construct functionalized five-membered rings, as well as nitrogen heterocycles in a single operation. The intramolecular cascade rearrangement allows for the direct and highly diastereoselective synthesis of azaspirocyclic natural product cores. Second, the cascade rearrangement will be applied to the synthesis of quaternary stereogenic centers. In the final objective, efforts will be directed at achieving an enantioselective cascade rearrangement.Professor Javier Read de Alaniz will also work with outreach programs at the University of California Santa Barbara to help overcome the lack of minority representation in the sciences. Professor Read de Alaniz will serve as the faculty advisor for the University of California Leadership Excellence through Advanced Degrees (UC LEADS) program. Working with the UC LEADS program Professor Read de Alaniz will participate in and lead a series of professional development workshop for promising underrepresented minority undergraduate students during the summer. The second educational initiative will provide students with the opportunity to interact with postdoctoral research associates and faculty from underrepresented minority/female backgrounds in an organized, yet casual, brown-bag lunch forum. Faculty/post-doctoral research associates will discuss their career pathes along with topics of isolation and language barriers, increasing diversity on the campus, labeling, peer misperceptions, and mentoring.