P-58 ザラゴジン酸類の合成研究(ポスター発表の部)
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Zaragozic acids (squalestatins), a family of structurally related fungal metabolites isolated from different organisms by three independent groups in 1992, have been found to be potent inhibitor of squalene synthase and farnesyl-protein transferase. These compounds share a common highly oxygenated hydrophilic core and differ in two lipophilic side chains (e.g., zaragozic acid A (1)). A number of reports for synthesis of them was reflected their unique structures and biological activities. The most characteristic feature of them is the 2,8-dioxabicyclo[3.2.1]-octane core bearing six contiguous chiral carbon atoms. Total syntheses of zaragozic acids have been reported, however, various synthetic approaches are investigated continuously. Here we would like to report a new synthetic route for construction of the core moiety of zaragozic acids from furan derivative. This synthesis involves two crucial steps of regio- and stereoselective introduction of oxygen functionalities into C(3), C(4), C(6) and C(7) position on 7-oxabicyclo[2.2.1]hepta-2,5-diene derivative 5 (Scheme 1) and one-pot Grob fragmentation-reduction-iodo acetalization reaction of 7-oxabicyclo[2.2.1]heptane 20 to give 2,8-dioxabicyclo[3.2.1]-octane ring system 23 (Scheme 3). Enantioselective syntheses of the important intermediate (-)-8 by use of hydrolysis of symmetrical diester 6 with pig liver esterase (PLE) to give 26 and of side chain moiety 34 were also achieved as shown in Scheme 4 and Scheme 5, respectively.
- 天然有機化合物討論会の論文
- 2008-09-01
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