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- W2082051207 endingPage "5288" @default.
- W2082051207 startingPage "5276" @default.
- W2082051207 abstract "In this study, we report the first total synthesis and complete stereostructure of gambieric acid A, a potent antifungal polycyclic ether metabolite, in detail. The A/B-ring exocyclic enol ether 32 was prepared through a Suzuki–Miyaura coupling of the B-ring vinyl iodide 18 and the alkylborate 33 and subsequent closure of the A-ring by using diastereoselective bromoetherification as the key transformation. Suzuki–Miyaura coupling of 32 with acetate-derived enol phosphate 49, followed by ring-closing metathesis of the derived diene, produced the D-ring. Subsequent closure of the C-ring through a mixed thioacetalization completed the synthesis of the A/BCD-ring fragment 8. The A/BCD- and F′GHIJ-ring fragments (i.e., 8 and 9) were assembled through Suzuki–Miyaura coupling. The C25 stereogenic center was elaborated by exploiting the intrinsic conformational property of the seven-membered F′-ring. After the oxidative cleavage of the F′-ring, the E-ring was formed as a cyclic mixed thioacetal (i.e., 70) and then stereoselectively allylated by using glycosylation chemistry. Ring-closing metathesis of the diene 3 thus obtained closed the F-ring and completed the polycyclic ether skeleton. Finally, the J-ring side chain was introduced by using a Julia–Kocienski olefination in the presence of CeCl3 to complete the total synthesis of gambieric acid A (1), thereby unambiguously establishing its complete stereostructure. The present total synthesis enabled us to evaluate the antifungal and antiproliferative activities of 1 and several synthetic analogues." @default.
- W2082051207 created "2016-06-24" @default.
- W2082051207 creator A5013904629 @default.
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- W2082051207 creator A5048373541 @default.
- W2082051207 creator A5077476218 @default.
- W2082051207 creator A5084478484 @default.
- W2082051207 date "2013-03-28" @default.
- W2082051207 modified "2023-09-27" @default.
- W2082051207 title "Total Synthesis and Biological Evaluation of (+)-Gambieric Acid A and Its Analogues" @default.
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