Bio

Honors & Awards


  • Graduate Research Fellowship, National Science Foundation (2014-2017)

Education & Certifications


  • B.A., Reed College, Biochemistry & Molecular Biology (2011)

Research & Scholarship

Lab Affiliations


Publications

Journal Articles


  • Dyotropic Rearrangements of Fused Tricyclic beta-Lactones: Application to the Synthesis of (-)-Curcumanolide A and (-)-Curcumalactone JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Leverett, C. A., Purohit, V. C., Johnson, A. G., Davis, R. L., Tantillo, D. J., Romo, D. 2012; 134 (32): 13348-13356

    Abstract

    Dyotropic rearrangements of fused, tricyclic ?-lactones are described that proceed via unprecedented stereospecific, 1,2-acyl migrations delivering bridged, spiro-?-butyrolactones. A unique example of this dyotropic process involves a fused bis-lactone possessing both ?- and ?-lactone moieties which enabled rapid access to the core structures of curcumanolide A and curcumalactone. Our current mechanistic understanding of the latter dyotropic process, based on computational studies, is also described. Other key transformations in the described divergent syntheses of (-)-curcumanolide A and (-)-curcumalactone from a common intermediate (11 and 12 steps from 2-methyl-1,3-cyclopentanedione, respectively), include a catalytic, asymmetric nucleophile (Lewis base)-catalyzed aldol-lactonization (NCAL) leading to a tricyclic ?-lactone, a Baeyer-Villiger oxidation in the presence of a ?-lactone, and highly facial-selective and stereocomplementary reductions of an intermediate spirocyclic enoate. The described dyotropic rearrangements significantly alter the topology of the starting tricyclic ?-lactone, providing access to complex spirocyclic cyclopentyl-?-lactones and bis-?-lactones in a single synthetic operation.

    View details for DOI 10.1021/ja303414a

    View details for Web of Science ID 000307487200039

    View details for PubMedID 22853802

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