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Pd(0)-Catalyzed C(sp3)-H Activation for the Synthesis of Natural Products and Cyclopropanes

Thesmar, Pierre. Pd(0)-Catalyzed C(sp3)-H Activation for the Synthesis of Natural Products and Cyclopropanes. 2021, Doctoral Thesis, University of Basel, Faculty of Science.

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Abstract

C-H bonds are ubiquitous in organic substances. That is why, over the past decades, the transition metal-catalyzed intramolecular activation of unactivated C-H bonds has emerged as a powerful tool for synthetic chemists. In particular, selective activation and functionalization of C-H bonds allows a straightforward access to high molecular complexity in an atom- and step-economical fashion and without the need from extensive functionalization of the starting materials.
Our research group being specialized in this particular field, my PhD thesis has been focused on the application of Pd(0)/Pd(II) catalyzed C(sp3)-H activation methods for the total synthesis of complex natural products, along with the development of new methodologies using this approach.
In the first part of this thesis, we report the enantioselective, scalable and divergent total synthesis of two complex dithiodiketodipiperazine natural products (–)-epicoccin G and (–)-rostratin A using a double Pd(0)-catalyzed C(sp3)-H activation strategy.
In the second part of this thesis, we present a new synthetic method to access cyclopropanes using remote functionalization of distal C-H bonds. Overall, taking advantage of the Pd-1,4 shift reactivity, cyclopropanation reaction was performed from intramolecular double C(sp3)-H activation on gem-dialkyl groups, which has been considered for long as an elusive transformation.
Advisors:Baudoin, Olivier and Tiefenbacher, Konrad Karl and Carreira, Eric
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier
Item Type:Thesis
Thesis Subtype:Doctoral Thesis
Thesis no:14042
Thesis status:Complete
Number of Pages:624
Language:English
Identification Number:
  • urn: urn:nbn:ch:bel-bau-diss140422
edoc DOI:
Last Modified:26 Mar 2021 05:30
Deposited On:25 Mar 2021 08:45

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