Synthesis of Heterocyclic Natural Products

合成有机化学项目将支持宾夕法尼亚州立大学化学系Steven M. Weinreb博士的研究。Weinreb博士将开发合成杂环的新方法，杂环是在许多复杂结构中发现的一种重要的化学结构。在现代农业和医学中使用的许多物质中都发现了这些物质。研究了基于n -亚砜基亲二酚diols - alder环加成的合成方法和天然产物的全合成。该方法将具体应用于Nuphar生物碱7-epi- anhydroonupharidine的合成。此外，分子内版本的程序将用于立体选择性合成邻二胺在一个新的全合成自旋霉素。这是抗生素自旋霉素和结核放线菌素的一种成分，将用于高效合成链霉素，链霉素是链霉素类抗生素的一员。立体选择性合成维生素生物素也将开发使用这种Diels-Alder为基础的方法。研究了环双亚胺金属化法合成邻二胺的新工艺。为了有效地合成饱和氮杂环，我们将研究Heck反应的一种新变体。此外，将研究由炔和二氧化碳衍生的镍金属循环，以发展一些普遍有用的合成方法。这些金属环将被用作β -酰基乙烯阴离子，它们与几种类型的亲电试剂的反应将被测试。

The Synthetic Organic Chemistry Program will be supporting the research of Dr. Steven M. Weinreb of the Department of Chemistry at Pennsylvania State University. Dr. Weinreb will be developing new methods of synthesizing heterocyles, an important type of chemical structure found in many complex structures. These are found in many of the substances used in modern agriculture and medicine. Synthetic methodology and natural product total synthesis based upon N-sulfinyl dienophile Diels-Alder cycloadditions will be pursued. The methodology will specifically be applied to synthesis of the Nuphar alkaloid 7-epi-anhydronupharidine. In addition, an intramolecular version of the procedure will be utilized for the stereoselective synthesis of vicinal diamines in a new total synthesis of capreomycidine. This is a component of the antibiotics capreomycine and the tuberactinomycidines, and will be used in an efficient synthesis of streptolidine, which is a member of the streptothricin antibiotics. A stereoselective synthesis of the vitamin biotin will also be developed using this Diels-Alder based methodology. A new procedure for synthesis of vicinal diamines will be investigated via metallation of cyclic bis-imines. A novel variation of the Heck reaction will be studied in order to efficiently synthesize saturated nitrogen heterocycles. Moreover, nickel metallacycles derived from alkynes and carbon dioxide will be investigated in order to develop some generally useful synthetic methodology. These metallacycles will be utilized as beta-acylvinyl anions and their reactions with several types of electrophiles will be tested.