Title:
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
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