Title:
Organic syntheses: Modular divergent formation of anti-malarial natural products
Organic syntheses: Modular divergent formation of anti-malarial natural products
dc.contributor.advisor | France, Stefan | |
dc.contributor.advisor | Kubanek, Julia | |
dc.contributor.author | Osborne-Benthaus, Kymberlee Alana | |
dc.contributor.committeeMember | Kelly, Wendy | |
dc.contributor.committeeMember | Collard, David | |
dc.contributor.department | Chemistry and Biochemistry | |
dc.date.accessioned | 2018-05-31T18:12:32Z | |
dc.date.available | 2018-05-31T18:12:32Z | |
dc.date.created | 2018-05 | |
dc.date.issued | 2018-01-22 | |
dc.date.submitted | May 2018 | |
dc.date.updated | 2018-05-31T18:12:32Z | |
dc.description.abstract | Callophycus serratus, a Fijian red macro alga, is the source of an interesting family of macrolides which have been elusive to the synthetic community. Sesquiterpene bromophycolides P, Q U, and related callophycolide A have highly conserved structural motifs which can be accessed through similar transformations therefore allowing for the application of a modular strategy. Formation of the modules features an expansion of electrophilic π-cyclizations with bromodiethylsulfonium bromopentachloroantimonate(V) (BDSB), and stereoselective Sharpless epoxidation and dihydroxylation conditions. Connection of the modules entail optimization of a magnesate assisted aryl-allyl coupling and a sulfone stabilized anion epoxide ring opening. The strategies explored can be applied to access a family of approximately 30 molecules. The development of a synthetic strategy is desirable due to notable anti-bacterial (MRSA and VREF), anti-malarial properties, and low natural abundance. Herein, I report results for the progress towards the total synthesis of bromophycolides P, Q, U, and callophycolide A utilizing a modular strategy. | |
dc.description.degree | M.S. | |
dc.format.mimetype | application/pdf | |
dc.identifier.uri | http://hdl.handle.net/1853/59841 | |
dc.language.iso | en_US | |
dc.publisher | Georgia Institute of Technology | |
dc.subject | Natural products | |
dc.subject | Organic chemistry | |
dc.subject | Synthesis | |
dc.subject | Anti-malarial | |
dc.subject | Callophycus serratus | |
dc.subject | Bromophycolide | |
dc.subject | Callophycolide | |
dc.title | Organic syntheses: Modular divergent formation of anti-malarial natural products | |
dc.type | Text | |
dc.type.genre | Thesis | |
dspace.entity.type | Publication | |
local.contributor.advisor | France, Stefan | |
local.contributor.advisor | Kubanek, Julia | |
local.contributor.corporatename | School of Chemistry and Biochemistry | |
local.contributor.corporatename | College of Sciences | |
local.relation.ispartofseries | Master of Science in Chemistry | |
relation.isAdvisorOfPublication | 60127d9c-be17-4aa7-bd28-c94458c4a043 | |
relation.isAdvisorOfPublication | 89259fc4-6fa4-4edf-9919-baccdcb6f1a1 | |
relation.isOrgUnitOfPublication | f1725b93-3ab8-4c47-a4c3-3596c03d6f1e | |
relation.isOrgUnitOfPublication | 85042be6-2d68-4e07-b384-e1f908fae48a | |
relation.isSeriesOfPublication | 8954817e-f914-4a18-bccd-8e0ecaf17c10 | |
thesis.degree.level | Masters |