Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/38768
Title: Synthetic Studies to Bielschowskysin Macrocyclic Precursors
Authors: KARTHIK SEKAR
Keywords: GPI anchor, inositol resolution, arabinomannan analogues, Bielschowskysin, 2+2 photochemical, Macrocycliic precursor
Issue Date: 21-Dec-2011
Source: KARTHIK SEKAR (2011-12-21). Synthetic Studies to Bielschowskysin Macrocyclic Precursors. ScholarBank@NUS Repository.
Abstract: Malaria is a vector borne disease that is transmitted by mosquito species like Plasmodium falciparum (Pf). In the first part of this PhD work, synthetic studies to the malarial (Pf) glycophosphatidyl inositol (GPI) anchor 1 and lipoarabinomannan glycolipids will be detailed. Our (3+3) strategy to construct the GPI malarial candidate and a one-pot trimannoside, synthesized by an iterative glycosyslation strategy, will be highlighted. Furthermore, the convenient resolution of myo-inositol was achieved by a direct glucosidation method. Arabinomannan analogues were synthesized by dibutyl phosphate coupling strategy between a mannose orthoester and a 5-hydroxyl free arabinofuranoside. The synthesis was accomplished by global debenzylation and the target compounds submitted for biological studies. In the second part of this PhD work, synthetic studies to macrocyclic precursors of bielschowskysin 2, an antimalarial anticancer lead, will be presented. Several scalable left and right fragments were synthesized from L-malic acid, D-glucose, and L-tartaric acid. Coupling strategies of these building blocks followed by macrocyclisation attempts towards the cembrane macrocycle of the bielschowskysin were also pursued.
URI: http://scholarbank.nus.edu.sg/handle/10635/38768
Appears in Collections:Ph.D Theses (Open)

Show full item record
Files in This Item:
File Description SizeFormatAccess SettingsVersion 
Title page.pdf5.91 kBAdobe PDF

OPEN

NoneView/Download
ack & TOC.pdf242.08 kBAdobe PDF

OPEN

NoneView/Download
Part A.pdf3.84 MBAdobe PDF

OPEN

NoneView/Download
Part A NMR spectra.pdf4.37 MBAdobe PDF

OPEN

NoneView/Download
Part B title page.pdf159.1 kBAdobe PDF

OPEN

NoneView/Download
Part B.pdf6.58 MBAdobe PDF

OPEN

NoneView/Download
Part B NMR Spectra.pdf6.68 MBAdobe PDF

OPEN

NoneView/Download

Page view(s)

146
checked on Dec 11, 2017

Download(s)

681
checked on Dec 11, 2017

Google ScholarTM

Check


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.