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Total synthesis of (-)-pyridovericin and synthetic studies towards aetheramide B

Schmid, Fabian Felix. Total synthesis of (-)-pyridovericin and synthetic studies towards aetheramide B. 2015, PhD Thesis, University of Basel, Faculty of Science.

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Official URL: http://edoc.unibas.ch/diss/DissB_11331

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Abstract

In this thesis, two projects involving the total synthesis of natural products are presented.
The first part gives an overview on neurodegenerative diseases and introduces the
neuritogenic pyridopolyene natural product (–)-pyridovericin. The enantioselective total
synthesis of (–)-pyridovericin is presented. The key steps were an enantioselective,
iridium-catalyzed hydrogenation of an enoate and an E-selective Horner-Wadsworth-
Emmons reaction. The complex pyridopolyene structure was then truncated and the
neuritogenic core structure identified. Truncated natural product analogs were
synthesized and successfully implemented in a neuritogenic surface material.
The second part reviews the current state of research on HIV and AIDS. Our efforts
towards the total synthesis of the recently isolated HIV-inhibitory natural product
aetheramide B are reported. Three advanced building blocks were synthesized
enantioselectively in good yields. The key steps involved the enantioselective
hydrogenation of an enamide to form an amino ester, the diastereoselective alkynylation
of a homobenzylic aldehyde and the enantioselective reduction of a bromoenone. The
building blocks were then successfully coupled to form the macrocyclic depsipeptide
core structure. The macrocyclic core of aetheramide B was then synthesized in a
macrolactonization reaction.
Advisors:Gademann, Karl
Committee Members:Pfaltz, Andreas
Faculties and Departments:05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Chemie (Gademann)
Item Type:Thesis
Thesis no:11331
Bibsysno:Link to catalogue
Number of Pages:269 S.
Language:English
Identification Number:
Last Modified:30 Jun 2016 10:57
Deposited On:10 Sep 2015 08:37

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