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

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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.