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Total Synthesis of Complex Terpene Natural Products

复杂萜类天然产物的全合成

基本信息

批准号：
1954319
负责人：
Seth Herzon
金额：
$ 38.21万
依托单位：
Yale University
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2020
资助国家：
美国
起止时间：
2020-04-15 至 2025-03-31
项目状态：
未结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1954319&HistoricalAwards=false
关键词：
Total Synthesis Complex Terpene Natural

项目摘要

With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Seth B. Herzon in the Department of Chemistry at Yale University. The research focuses on the creation of complex molecules, known as natural products, in the laboratory. A natural product is a chemical compound or substance produced by a living organism—that is, found in nature. The researchers are developing new reactions to achieve the conversion of one chemical to another in unprecedented ways. Access to these molecules allows the researchers to study their properties, including their biological activities. The natural products are essential to the chemical industries (pharmaceutical, fine and industrial chemicals). The training the students receive provides them with the skillset needed to pursue STEM careers. Yale University’s location in downtown New Haven uniquely positions the Professor Herzon to conduct STEM outreach with pre-college students from underrepresented and/or disadvantaged backgrounds. He participates in public science demonstrations and mentoring activities, providing hands-on laboratory experiences for local high school students. The research team designs and implements these educational outreach activities into Yale’s Pathways to Science Program, which has helped Yale faculty connect with over 1500 high school students.This research focuses on the total synthesis of euonyminol/cathedulin and rearranged pimarane terpenes. Professor Herzon is progressing toward the synthesis of both classes of targets. This research is focused on completing the synthesis of euonyminol and elaborating this to cathedulins. A central element of the work involves a late-stage directed C–H bond oxidation, which may lead to novel methods for C–H activation. The scope of a novel oxyalkylation of allylic alcohols discovered en route to euonyminol is being evaluated, and attempts to render this process enantioselective are being pursued. The research team is also focused on completing the synthesis of the rearranged pimarane diterpene diaporthein B. The laboratory is utilizing an advanced intermediate that contains all of the necessary rings and a key bridgehead quaternary center of the target. A new carbonylative Stille coupling of hydroxymethylstannanes, developed en route to diaporthein B, is being developed. The application of the strategies developed herein to other related natural products is being evaluated.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

有了这个奖项，NSF化学部的化学合成计划正在支持Seth B教授的研究。耶鲁大学化学系的Herzon说。该研究的重点是在实验室中创造复杂的分子，即天然产物。天然产物是由生物体产生的化合物或物质，即在自然界中发现的化合物或物质。研究人员正在开发新的反应，以前所未有的方式将一种化学物质转化为另一种化学物质。获得这些分子使研究人员能够研究它们的特性，包括它们的生物活性。天然产品对化学工业（制药、精细化学品和工业化学品）至关重要。学生接受的培训为他们提供了追求STEM职业所需的技能。耶鲁大学在纽黑文市中心的位置独特的定位教授Herzon进行STEM外展与来自代表性不足和/或弱势背景的大学预科学生。他参与公共科学示范和指导活动，为当地高中生提供动手实验室经验。该研究团队设计并实施了这些教育推广活动到耶鲁大学的科学之路计划，该计划已帮助耶鲁大学教师与1500多名高中生建立了联系。本研究的重点是Euonyminol/cathedulin和重排的pimarane萜烯的全合成。 Herzon教授正朝着合成这两类目标的方向发展。本研究的重点是完成Euonyminol的合成，并将其加工成cathedulins。这项工作的一个中心内容涉及后期定向C-H键氧化，这可能导致C-H活化的新方法。一种新的烷氧基化的烯丙醇的路线上发现的Euonyminol的范围正在评估，并试图使这一过程的对映选择性正在进行中。研究小组还专注于完成重排的海松烷二萜diaporthein B的合成。该实验室正在利用一种先进的中间体，其中包含所有必要的环和目标的关键桥头四元中心。正在开发一种新的羟甲基锡烷的羰基化Stille偶联，该偶联是在合成diaporthein B的过程中开发的。该奖项反映了NSF的法定使命，并被认为值得通过使用基金会的知识价值和更广泛的影响审查标准进行评估的支持。

项目成果

期刊论文数量（2）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

An oxidative photocyclization approach to the synthesis of Securiflustra securifrons alkaloids

DOI：
10.1126/science.adl6163
发表时间：
2024-02
期刊：
Science
影响因子：
56.9
作者：
Brandon W. Alexander;Noah M. Bartfield;Vaani Gupta;Brandon Q. Mercado;Mark Del Campo;Seth B. Herzon-
通讯作者：
Brandon W. Alexander;Noah M. Bartfield;Vaani Gupta;Brandon Q. Mercado;Mark Del Campo;Seth B. Herzon-

Enantioselective Synthesis of Euonyminol

卫矛醇的对映选择性合成