Brendyn P. Smith

ORCID: 0009-0006-4619-9547
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About
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Research Areas
  • Oxidative Organic Chemistry Reactions
  • Traditional and Medicinal Uses of Annonaceae
  • Organic Chemistry Cycloaddition Reactions
  • Polyoxometalates: Synthesis and Applications
  • Catalytic C–H Functionalization Methods
  • Marine Sponges and Natural Products
  • X-ray Diffraction in Crystallography
  • Crystallization and Solubility Studies
  • Cyclopropane Reaction Mechanisms

Scripps Research Institute
2024

Torrey Pines Institute For Molecular Studies
2024

Scripps (United States)
2024

Scripps Institution of Oceanography
2024

Michigan State University
2023

Abstract The first total synthesis of dragocins A−C, remarkable natural products containing an unusual C4’ oxidized ribose architecture bridged by a polyhydroxylated pyrrolidine, is presented through route featuring number uncommon maneuvers. Several generations towards the target molecules are presented, including spectacular failure key C−H oxidation on late‐stage intermediate. final features rapid, stereocontrolled access to densely functionalized pyrrolidine and unprecedented...

10.1002/anie.202401107 article EN Angewandte Chemie International Edition 2024-02-15

Abstract The first total synthesis of dragocins A−C, remarkable natural products containing an unusual C4’ oxidized ribose architecture bridged by a polyhydroxylated pyrrolidine, is presented through route featuring number uncommon maneuvers. Several generations towards the target molecules are presented, including spectacular failure key C−H oxidation on late‐stage intermediate. final features rapid, stereocontrolled access to densely functionalized pyrrolidine and unprecedented...

10.1002/ange.202401107 article EN Angewandte Chemie 2024-02-15

The first total synthesis of dragocins A–C, remarkable natural products containing an unusual C-4’oxidized ribose architecture bridged by a polyhydroxylated pyrrolidine, is presented through route featuring number uncommon maneuvers. Several generations towards the target molecules are including spectacular failure key C–H oxidation on late- stage intermediate. final features rapid, stereocontrolled access to densely functionalized pyrrolidine and unprecedented diastereoselective oxidative...

10.26434/chemrxiv-2024-mvf2m preprint EN cc-by 2024-01-03

Two epoxidation catalysts one of which consists two VANOL ligands and an aluminum the other a boron were compared. Both are highly effective in catalytic asymmetric variety aromatic aliphatic aldehydes with diazoacetamides giving high yields excellent inductions. The catalyst is at 0 °C –40 °C. Although both (R)-VANOL give very inductions (up to 99% ee), they opposite enantiomers epoxide. mechanism, rate- enantioselectivity-determining step, origin enantiodivergence evaluated using DFT calculations.

10.26434/chemrxiv-2023-cdpqb preprint EN cc-by 2023-05-08

Two epoxidation catalysts, one of which consists two VANOL ligands and an aluminum the other that a boron, were compared. Both catalysts are highly effective in catalytic asymmetric variety aromatic aliphatic aldehydes with diazoacetamides, giving high yields excellent inductions. The catalyst is at 0 °C boron -40 °C. Although both (R)-VANOL give very inductions (up to 99% ee), they opposite enantiomers epoxide. mechanism, rate- enantioselectivity-determining step, origin enantiodivergence...

10.1021/acscatal.3c03929 article EN ACS Catalysis 2023-09-25
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