Strategic Approaches to Cycloheptanoid Natural Products

有机合成化学是由寻找有效的方法从现成的起始材料构建碳基分子的持续需求驱动的。加州理工学院的Brian Stoltz教授获得了这个奖项，他使用了以前从未用于此目的的新方法合成了两种复杂的天然分子。这类分子可能对社会有益，特别是作为治疗癌症等使人衰弱和危及生命的疾病的药物。该研究小组还在研究制造其他重要碳基分子的新方法。Stoltz教授大力支持各种旨在教育和激励未来科学家的外展项目。有了这个奖项，他将在他的实验室为优秀学生提供暑期本科生研究职位，并在当地小学提供科学演示。诸如此类的推广项目鼓励那些在科学领域代表性不足的群体的参与。Stoltz教授正在探索合成两种结构有趣的天然产物的各种策略，即鞘内酯A和curcusone c。这些目标的完全合成尚未报道。虽然不同，但这些化合物有几个共同的结构特征，这些特征在智力水平上与项目相关。最值得注意的是，这两种靶标都含有碳基多环框架，分别具有环庚烷环的外围或中心熔接。甲磺内酯的[5,6,7]-三环骨架是通过闭合环复分解（RCM）和跨环diols - alder策略构建的，而甲磺内酯C的[5,7,6]核心是通过交叉亲电偶联和michael型环化合成的。Stoltz教授和他的学生目前正在开展各种推广活动，以鼓励有才华的青年科学家探索类似的项目。该奖项反映了美国国家科学基金会的法定使命，并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，被认为值得支持。

Organic synthetic chemistry is driven by the ongoing need to find efficient ways to construct carbon-based molecules from readily available starting materials. With this award, Professor Brian Stoltz at Caltech is synthesizing two complex naturally occurring molecules using novel approaches that have not been previously utilized for this purpose. These classes of molecules can be of benefit to society, particularly as medicinal agents in the treatment of debilitating and life-threatening diseases such as cancer. The research team is also studying new methods for making other important carbon-based molecules. Professor Stoltz strongly supports a variety of outreach programs with the intent of teaching and inspiring future scientists. With this award he is offering summer undergraduate research positions in his laboratory for exceptional students and providing science demonstrations at local elementary schools. Outreach programs such as these encourage participation from groups that are otherwise underrepresented in the sciences.Professor Stoltz is exploring various strategies for the syntheses of two structurally intriguing natural products, namely scabrolide A and curcusone C. The total syntheses of these targets have not yet been reported. Although distinct, these compounds have several common structural features that relate the project at an intellectual level. Most notably, both targets contain a carbon-based polycyclic framework possessing either a peripherally-fused or centrally-fused cycloheptane ring, respectively. The [5,6,7]-tricyclic framework of scabrolide A is being constructed via a ring-closing metathesis (RCM) and transannular Diels-Alder strategy, whereas the [5,7,6] core of curcusone C is being synthesized by means of a cross-electrophile coupling and Michael-type annulation. Professor Stoltz and his students are currently engaged in various outreach activities in order to encourage talented young scientists to explore similar projects.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.