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Volumn 77, Issue 21, 2012, Pages 9574-9584

A unifying stereochemical analysis for the formation of halogenated C 15-acetogenin medium-ring ethers from laurencia species via intramolecular bromonium ion assisted epoxide ring-opening and experimental corroboration with a model epoxide

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; EPOXIDE RING-OPENING REACTION; MEDIUM-RING ETHER; NATURAL PRODUCTS; RING OPENING; STEREOCHEMICAL ANALYSIS;

EID: 84868350378     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301580c     Document Type: Article
Times cited : (30)

References (96)
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    • For a review, see: In; Barton, D. H. R. Meth-Cohn, O. Nakinishi, K. Elsevier: Oxford, Vol.
    • For a review, see: Murai, A. In Comprehensive Natural Products Chemistry; Barton, D. H. R.; Meth-Cohn, O.; Nakinishi, K., Eds.; Elsevier: Oxford, 1999; Vol. 1, pp 303-324.
    • (1999) Comprehensive Natural Products Chemistry , vol.1 , pp. 303-324
    • Murai, A.1
  • 67
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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 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
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 15898-15901
    • Snyder, S.A.1    Treitler, D.S.2    Brucks, A.P.3    Sattler, W.4
  • 74
    • 84867832886 scopus 로고    scopus 로고
    • For the intramolecular capture of a bromonium ion by the oxygen of an oxetane, see
    • For the intramolecular capture of a bromonium ion by the oxygen of an oxetane, see: Keshipeddy, S.; Martínez, I.; Castillo, B. F., II; Morton, M. D.; Howell, A. R. J. Org. Chem. 2012, 77, 7883-7890
    • (2012) J. Org. Chem. , vol.77 , pp. 7883-7890
    • Keshipeddy, S.1    Martínez, I.2    Castillo, B.F.I.I.3    Morton, M.D.4    Howell, A.R.5
  • 75
    • 78650891151 scopus 로고    scopus 로고
    • For an intramolecular bromonium ion assisted epoxide ring-opening reaction with capture of the oxonium ion with an added external nucleophile, see
    • 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
    • (2011) J. Org. Chem. , vol.76 , pp. 97-104
    • Bonney, K.J.1    Braddock, D.C.2    White, A.J.P.3    Yaqoob, M.4
  • 76
    • 33846182254 scopus 로고    scopus 로고
    • 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
    • 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
    • (2006) Org. Lett. , vol.8 , pp. 6055-6058
    • Braddock, D.C.1
  • 77
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    • The (12 Z)-geometrical laurediol isomer has been isolated from Laurencia species
    • The (12 Z)-geometrical laurediol isomer has been isolated from Laurencia species: Fukuzawa, A.; Honma, T.; Takasugi, Y.; Murai, A. Phytochemistry 1993, 32, 1435-1438
    • (1993) Phytochemistry , vol.32 , pp. 1435-1438
    • Fukuzawa, A.1    Honma, T.2    Takasugi, Y.3    Murai, A.4
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    • For a representative example see
    • For a representative example see: Miyaoka, H.; Tamura, M.; Yamada, Y. Tetrahedron 2000, 56, 8083-8094
    • (2000) Tetrahedron , vol.56 , pp. 8083-8094
    • Miyaoka, H.1    Tamura, M.2    Yamada, Y.3
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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
    • 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
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 7690-7692
    • Mihelich, E.D.1    Daniels, K.2    Eickhoff, D.J.3
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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
    • (2011) Org. Lett. , vol.13 , pp. 2690-2693
    • Gutierrez-Cepeda, A.1    Fernandez, J.J.2    Norte, M.3    Souto, M.L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.