Chemistry is truly the central science and underpins much of the efforts of scientists and engineers to improve life for humankind. TheMIT Department of Chemistryis taking a leading role in discovering new chemical synthesis, catalysis, creating sustainable energy, theoretical and experimental understanding of chemistry, improving the environment, detecting and curing disease, developing materials new properties, and nanoscience.
The Chemistry Education Office staff is responsible for administering the educational programs in the Department of Chemistry. Students can find answers to many questions about the undergraduate and graduate programs on the department website, and they are encouraged to stop by and see the staff in the office located in 6-205.
The student-run outreach programs in the Department of Chemistry aim to bring the excitement of chemical sciences to the community through lively demonstrations designed to illustrate a broad range of chemical principles. Graduate students visit science classes in high schools and middle schools in the Greater Boston area with a view to demystifying chemistry through hands-on experiments. ClubChem, an undergraduate chemistry organization, conducts Chemistry Magic Shows for elementary schools and youth programs in the Greater Boston area.
Chemistry is truly the central science and underpins much of the efforts of scientists and engineers to improve life for humankind. MIT Chemistry is taking a leading role in discovering new chemical synthesis, catalysis, creating sustainable energy, theoretical and experimental understanding of chemistry at its most fundamental level, unraveling the biochemical complexities of natural systems, improving the environment, detecting and curing disease, developing materials new properties, and nanoscience.
ABSTRACT: We report the first total syntheses of (+)- haplocidine, and its N1-amide congener (+)-haplocine. Our concise synthesis of these alkaloids required the development of a late-stage and highly selective C–H oxidation of complex aspidosperma alkaloid derivatives. A versatile, amide directed orthoacetoxylation of indoline amides enabled our implementation of a unified strategy for late-stage diversification of hexacyclic C19-hemiaminal ether structures via oxidation of the corresponding pentacyclic C19-iminium ions. An electrophilic amide activation of a readily available C21-oxygenated lactam, followed by transannular cyclization and in situ trapping of a transiently formed C19-iminium ion, expediently provided access to hexacyclic C19-hemiaminal ether alkaloids (+)-fendleridine, (+)- acetylaspidoalbidine, and (+)-propionylaspidoalbidine. A highly effective enzymatic resolution of a non-β-branched primary alcohol (E=22) allowed rapid preparation of both enantiomeric forms of a C21-oxygenated precursor for synthesis of these aspidosperma alkaloids. Our synthetic strategy provides succinct access to hexacyclic aspidosperma derivatives, including the antiproliferative alkaloid (+)-haplocidine.