Convergent synthesis of the BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ethers |
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Authors: | Kazushi Sato |
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Institution: | Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan |
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Abstract: | A convergent synthesis of the nonacyclic BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ether marine natural products, has been achieved. The present synthesis involved as key features: (i) convergent union of the BCD- and GHIJ-ring fragments through esterification, (ii) construction of the E-ring as a lactone form via reductive acetylation, (iii) stereoselective allylation to establish the C26 stereocenter, and (iv) ring-closing metathesis reaction to form the nine-membered F-ring. |
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