서강대학교

초록/요약

PART Ⅰ. High-throughput Synthesis of 2-Substituted Methyl Benzo[b]furan-3-carboxylates without Transition Metal Catalyst. A highly effective and simple synthetic pathway for 2-substituted methyl benzo[b]furan-3-carboxylate was developed. Without expensive transition metals and very toxic carbon monoxide, it gave high yield of 2-substituted methyl benzofuran-3-carboxylate from commercially available 2-hydroxyphenylacetic acid and four synthetic steps. In addition, the new synthetic pathway did not require laborious purification procedure and gave pure products from simple recrystallization in most cases. PART Ⅱ. Synthesis of ADIBO and trans-Cyclooctene for Bioconjugation Chemistry. A bio-linker bearing ADIBO and triazolium moiety was synthesized. This biolinker has ADIBO moiety which can be used for ligating with biomolecule bearing azide group without copper catalysts. This biolinker also has triazolium and tosylate moiety which provide hydrophilicity and additional functionalization and it can be used for biolinker such as F-18 based radiopharmaceuticals. A new synthetic pathway for trans-cyclooctene precursor was also discovered. Compounds bearing trans-cyclooctene moiety is very important for various biorthogonal linker because it can be ligated with molecules containing tetrazine moiety without catalysts. We suggest new pathway for the synthesis of trans-4-Cyclooctenol as a trans-cyclooctene precursor and it can be used for synthesis of diasteromer-free-trans-cyclooctene compound.