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Synthetic studies of the Thio-Nazarov Cyclization, Biomimetic Total Syntheses of Shimalactones and Exiguamines, and Synthesis of Photoswitchable Dopamine Analogs

  • Author(s): Sofiyev, Vladimir
  • Advisor(s): Trauner, Dirk
  • Bergman, Robert G
  • et al.
Abstract

Synthetic studies of the Thio-Nazarov Cyclization

Biomimetic Total Syntheses of Shimalactones and Exiguamines

Synthesis of Photoswitchable Dopamine Analogs

Vladimir Sofiyev

Doctor of Philosophy in Chemistry

University of California, Berkeley

Professor Dirk Trauner, Co-Chair

Part 1 of this thesis describes progress towards thio-Nazarov electrocyclization utilizing substrates with a removable docking group, such as alkyl sulfides, for Lewis acid coordination. This work builds on the successful asymmetric catalysis of Nazarov electrocyclization using non-removable docking groups for coordination of Lewis acids.

Parts 2 and 3 of this thesis describe the biomimetic syntheses of the natural products shimalactones and exiguamines respectively. While the synthesis of alkaloids exiguamines A and B is an improvement of our previous work, the synthesis of polyketides shimalactones A and B is their first synthesis and describes a novel intramolecular addition of a b-ketolactone across a diene. Both syntheses feature pericyclic reactions in their key step biomimetic cascade reactions.

Part 4 of this thesis describes the synthesis of photoswitchable derivatives of dopamine, containing azobenzenes.

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