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Snyder has recently reported syntheses of halogenated 8- and 9-membered medium-ring ethers resembling those of the Laurencia acetogenins by a bromonium-induced ring expansion process involving intramolecular capture of a bromonium ion with the oxygen of a tetrahydrofuran and/or tetrahydropyran
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Snyder has recently reported syntheses of halogenated 8- and 9-membered medium-ring ethers resembling those of the Laurencia acetogenins by a bromonium-induced ring expansion process involving intramolecular capture of a bromonium ion with the oxygen of a tetrahydrofuran and/or tetrahydropyran: Snyder, S. A.; Treitler, D. S.; Brucks, A. P.; Sattler, W. J. Am. Chem. Soc. 2011, 133, 15898-15901
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For an intramolecular bromonium ion assisted epoxide ring-opening reaction with capture of the oxonium ion with an added external nucleophile, see: Bonney, K. J.; Braddock, D. C.; White, A. J. P.; Yaqoob, M. J. Org. Chem. 2011, 76, 97-104
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The natural products neoisoprelaurefucin (7-membered ring, see refs 3d and 7) and neolaurallene (9-membered ring, see refs 5c and 15) would arise from a (6 R,7 S)-configured epoxide instead of the (6 S,7 R)-epoxide of 19 by this analysis. The former epoxide has been invoked in the proposed biogenesis of the obtusallene family of natural products from Laurencia species
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The natural products neoisoprelaurefucin (7-membered ring, see refs 3d and 7) and neolaurallene (9-membered ring, see refs 5c and 15) would arise from a (6 R,7 S)-configured epoxide instead of the (6 S,7 R)-epoxide of 19 by this analysis. The former epoxide has been invoked in the proposed biogenesis of the obtusallene family of natural products from Laurencia species: Braddock, D. C. Org. Lett. 2006, 8, 6055-6058
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The e.r. of 30 was determined by chiral HPLC methods to be 78:22 (see the Supporting Information). This was achieved by tritylation of the primary alcohol and comparison with a racemic sample obtained by epoxidation of triene 29 (followed by tritylation) using 5 mol% vanadyl acetylacetonate and stoichiometric TBHP according to the method of Mihelich
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The e.r. of 30 was determined by chiral HPLC methods to be 78:22 (see the Supporting Information). This was achieved by tritylation of the primary alcohol and comparison with a racemic sample obtained by epoxidation of triene 29 (followed by tritylation) using 5 mol% vanadyl acetylacetonate and stoichiometric TBHP according to the method of Mihelich: Mihelich, E. D.; Daniels, K.; Eickhoff, D. J. J. Am. Chem. Soc. 1981, 103, 7690-7692
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Studies on bromonium ion induced transannular oxonium ion formation-fragmentation in model obtusallene systems (ref 27f), resulted in the formation of a [5.5.1]bicyclotridecane, and we speculated that it may represent the core of an undiscovered natural product from Laurencia species. New natural products with exactly this core have since been reported
-
Studies on bromonium ion induced transannular oxonium ion formation-fragmentation in model obtusallene systems (ref 27f), resulted in the formation of a [5.5.1]bicyclotridecane, and we speculated that it may represent the core of an undiscovered natural product from Laurencia species. New natural products with exactly this core have since been reported: Gutierrez-Cepeda, A.; Fernandez, J. J.; Norte, M.; Souto, M. L. Org. Lett. 2011, 13, 2690-2693
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