synthesis of hydroxylated muricatacin analogs related to squamocin
| Autor: | Tsai, Shih-Hung, 蔡世鴻 |
|---|---|
| Rok vydání: | 1999 |
| Druh dokumentu: | 學位論文 ; thesis |
| Popis: | 87 Two hydroxylated muricatacin analogs were synthesized in nine steps and the overall yield of 3 and 5 are 5.5% and 1.7%, respectively. This synthesis includes the addition of the starting aldehyde with acetylide, hydrogenation of the resulting propargylic alcohol using nickel boride as a catalyst, protection of the secondary hydroxyl group, deprotection of the primary hydroxyl group, oxidation of the primary alcohol to an aldehyde, addition of the aldehyde with vinyl magnasium bromide, orthoester Claisen rearrangement to the g,d-unsaturated ester, Sharpless asymmetric dihydroxylation and removal of the protecting group. The IC50 of compound 3 against the growth of human hepatocarcinoma cell lines (Hep G2 and 2, 2, 15) are 22.0 and 21.8 μM, respectively. |
| Databáze: | Networked Digital Library of Theses & Dissertations |
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