Beckman Center for Chemical Sciences

10550 N. Torrey Pines Road

La Jolla, CA   92037

email | phone: 858.784.8415

Unusual pharmacophoresChemical reactions underlie the biological mechanisms of many small molecules. Insight into chemical reactivity can therefore inform biology. Our laboratory has invented methods to easily access several classes of secondary metabolites that contain unique pharmacophores and whose covalent cellular reactivity is not understood. We are working to understand 1) the Nuphar dimers, which contain a covalently-reactive thiaspirane pharmacophore; 2. the asmarine alkaloids, whose N-hydroxydiazepine purine may bind metals, react covalently or oxidize a biomolecule; and 3. the isocyanoterpenes (ICTs), antimalarial marine metabolites whose isonitrile function may affect diverse bioinorganic processes. To study this latter class, we invented a general stereochemical inversion of tertiary alcohols. 

 

See publications: 

  1. Reiher, C. A.; Shenvi, R. A. "Stereocontrolled Synthesis of Kalihinol C" JACS, 2017, 139, 3647–3650.

  2. Jansen, D. J.; Shenvi, R. A. "Synthesis of (–)-Neothiobinupharidine", JACS, 2013, 135, 1209-1212.

  3. Wan, K. K.; Iwasaki, K.; Umotoy, J. C.; Wolan, D.; Shenvi, R. A. “Nitrosopurines en route to Potent Asmarine Cytotoxins” Angew. Chem. Int. Ed. 2015, 127, 2440-2445.

  4. Pronin, S. V.; Shenvi, R. A. “Synthesis of a Potent Antimalarial Amphilectene”, JACS. 2012, 134, 19604-19606.

  5. Pronin, S. V.; Reiher, C. A.; Shenvi, R. A. "Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines", Nature, 2013, 501, 195-199.

  6. Pronin, S. V.; Shenvi, R. A. “Synthesis of Highly Strained Terpenes by Nonstop Tail-to-Head Polycyclization”, Nature Chem. 2012, 4, 915-920.