Aminocyclitols have attracted a great deal of attention in recent years because of
diverse biological activities exhibited by them and also synthetic usefulness in the
synthesis of other natural compounds or pharmaceuticals. In this study, novel
synthetic strategies leading to aminocyclitol derivatives were investigated and the
synthesis of aminotetrol derivative (113) was achieved successfully. Moreover, by the
use of singlet oxygen reactions having considerable synthetic utilities in organic
chemistry we developed new synthetic methodologies for the aminoquercitol and
aminoconduritol derivatives (114 and 115). 3a,4,7,7a-tetrahydro-isobenzofuran-1,3-
dione (111) and 3a,7a-dihydro-isobenzofuran-1,3-dione (112) were synthesized from
easily available starting materials in order to be used as key compounds. The
anhydride moiety in key compounds provided us to obtain hydroxymethyl and amine
groups in target molecules by performing Curtius rearrangement. The introduction of
iii
hydroxyl groups into the molecules was achieved by both singlet oxygen and cisdihydroxylation
of osmium tetroxide. As a result of this, we were able to synthesize
aminotetrol derivative and we had considerable advance in the synthesis of
aminoconduritol and aminoquercitol derivatives.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.metu.edu.tr/upload/4/1050087/index.pdf |
| Date | 01 January 2003 |
| Creators | Ozturk, Nihal |
| Contributors | Balci, Metin |
| Publisher | METU |
| Source Sets | Middle East Technical Univ. |
| Language | English |
| Detected Language | English |
| Type | M.S. Thesis |
| Format | text/pdf |
| Rights | To liberate the content for public access |
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