Citation
Ashley, Eric Robert (2006) The First Total Synthesis of (–)-Lemonomycin and Progress toward the Total Synthesis of (+)-Cyanocycline A. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/QM4S-3B86. https://resolver.caltech.edu/CaltechETD:etd-11152005-155011
Abstract
The first total synthesis of (–)-lemonomycin has been accomplished. The synthesis features a novel, auxiliary-controlled asymmetric dipolar cycloaddition, a highly convergent Suzuki coupling, a diastereoselective enamide hydrogenation to set the C(3) stereochemistry, and a convergent, efficient, and completely diastereoselective Pictet-Spengler cyclization with a glycosyloxy acetaldehyde.
The total synthesis of (+)-cyanocycline A has been approached along two routes. Both routes feature dipolar cycloaddition reactions with alkyne-containing substrates and completely diastereoselective hydrogenations to set the C(4) stereochemistry. Proposals for the advancement of late-stage intermediates to the natural product are included.
Item Type: | Thesis (Dissertation (Ph.D.)) | ||||
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Subject Keywords: | Antibiotic; Antitumor; Dipolar Cycloaddition; Pictet-Spengler; Tetrahydroisoquinoline; Total Synthesis | ||||
Degree Grantor: | California Institute of Technology | ||||
Division: | Chemistry and Chemical Engineering | ||||
Major Option: | Chemistry | ||||
Awards: | Tobacco-Related Disease Research Program (TRDRP) Dissertation Award, 2002 | ||||
Thesis Availability: | Public (worldwide access) | ||||
Research Advisor(s): |
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Thesis Committee: |
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Defense Date: | 31 October 2005 | ||||
Record Number: | CaltechETD:etd-11152005-155011 | ||||
Persistent URL: | https://resolver.caltech.edu/CaltechETD:etd-11152005-155011 | ||||
DOI: | 10.7907/QM4S-3B86 | ||||
ORCID: |
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Default Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||
ID Code: | 4579 | ||||
Collection: | CaltechTHESIS | ||||
Deposited By: | Imported from ETD-db | ||||
Deposited On: | 17 Nov 2005 | ||||
Last Modified: | 08 Nov 2023 00:39 |
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