Escuela de Ciencias de la Salud Universidad Autónoma de Baja California Group Meeting Presentation Jesus Cordova Guerrero Olson Research Group January.

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Presentation transcript:

Escuela de Ciencias de la Salud Universidad Autónoma de Baja California Group Meeting Presentation Jesus Cordova Guerrero Olson Research Group January 29 th, 2016 Enantioselective Total Syntheses of Akuammiline Alkaloids (-)-Aspidophylline A, (+)-Strictamine,, and (-)-Cathafoline University of California Davis Moreno, J; Picazo, E.; Morrill, L. A.; Smith, J. M.; Garg, N. K. J. Am. Chem. Soc. 2016, ASAP

Escuela de Ciencias de la Salud Universidad Autónoma de Baja California University of California Davis Akuammiline family of alkaloids 2 Akuammiline alkaloids Furoindoline-type C5-oxidized-type Methanoquinolizidine-type Skelletally-rearranged Methanoquinolizidine-type Moreno, J; Picazo, E.; Morrill, L. A.; Smith, J. M.; Garg, N. K. J. Am. Chem. Soc. 2016, ASAP Eckermann, R.; Gaich, T. Synthesis 2013, 45,

Escuela de Ciencias de la Salud Universidad Autónoma de Baja California University of California Davis Akuammiline family of alkaloids 3 + (96% ee) Li’s cyclization Moreno, J; Picazo, E.; Morrill, L. A.; Smith, J. M.; Garg, N. K. J. Am. Chem. Soc. 2016, ASAP

Escuela de Ciencias de la Salud Universidad Autónoma de Baja California University of California Davis Akuammiline family of alkaloids 2

Escuela de Ciencias de la Salud Universidad Autónoma de Baja California University of California Davis Akuammiline family of alkaloids 5 + (96% ee) Li’s cyclization A tricyclic structure. Only one alkene present in the product. Intermediate: mixed acetal bearing an iodide. Second step: Ueno-Stork cyclization!!! Moreno, J; Picazo, E.; Morrill, L. A.; Smith, J. M.; Garg, N. K. J. Am. Chem. Soc. 2016, ASAP

Escuela de Ciencias de la Salud Universidad Autónoma de Baja California University of California Davis Akuammiline family of alkaloids 2

Escuela de Ciencias de la Salud Universidad Autónoma de Baja California University of California Davis Akuammiline family of alkaloids 7 Moreno, J; Picazo, E.; Morrill, L. A.; Smith, J. M.; Garg, N. K. J. Am. Chem. Soc. 2016, ASAP

Escuela de Ciencias de la Salud Universidad Autónoma de Baja California Thank you 8

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