메뉴 건너뛰기




Volumn 7, Issue 2, 2009, Pages 238-252

Erratum: Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscule (Organic & Biomolecular Chemistry (2009) 7 (238-252) DOI: 10.1039/b814953d);Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; POSITIVE IONS;

EID: 58149154535     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b922697b     Document Type: Erratum
Times cited : (35)

References (100)
  • 10
    • 33751003265 scopus 로고    scopus 로고
    • 15 halogenated 2,2′-bifuranyl natural products had been reported. A 2,2′-bifuranyl structure for elatenyne was considered less likely than the corresponding pyrano[3,2-b]pyran: J. G. Hall, Ph. D. Thesis, La Trobe University (Australia), 1984 For a summary of the advantages of two-directional synthesis see:
    • H. M. Sheldrake C. Jamieson J. W. Burton Angew. Chem., Int. Ed. 2006 45 7199
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 7199
    • Sheldrake, H.M.1    Jamieson, C.2    Burton, J.W.3
  • 18
    • 0003670973 scopus 로고    scopus 로고
    • Z. Rappoportand Y. Apeloig, John Wiley & Sons Ltd., New York, p. 1688 In model studies related to this project we have demonstrated that the intramolecular hydrosilation of glucose and galactose-derived exo-cyclic enol ethers gives rise to the corresponding 1,3-diols For the trans-selective hydroboration/oxidation of 6-membered exo-cyclic enol ethers see:
    • I. Ojima, Z.-J. Li, and J. Zhu, in The Chemistry of Organic Silicon Compounds, ed., Z. Rappoport, and, Y. Apeloig, John Wiley & Sons Ltd., New York, 1998, vol. 2 p. 1688
    • (1998) The Chemistry of Organic Silicon Compounds, Ed.
    • Ojima, I.1    Li, Z.-J.2    Zhu In, J.3
  • 32
    • 0033983302 scopus 로고    scopus 로고
    • 4-methanol to which 10 mol% acetyl chloride had been added. Beginning either with a mixture of the 2,2′-bifuranyls 15 or a 1: 1 mixture of 15: 9 gave the equilibrium ratios after 10 hours at room temperature which did not change after one week. In a separate experiment, a mixture of the pyrano[3,2-b]pyrans 9 also readily equilibrated to the same mixture of 15: 9 on stirring in acidic methanol. The pyrano[3,2-b]pyrans 9 exist as a 1: 1.3 mixture of diastereomers at equilibrium which is in keeping with the magnitude of the anomeric effect for 2-methoxytetrahydropyran in methanol see:
    • D. J. Kopecky S. D. Rychnovsky J. Org. Chem. 2000 65 191
    • (2000) J. Org. Chem. , vol.65 , pp. 191
    • Kopecky, D.J.1    Rychnovsky, S.D.2
  • 33
    • 0001339474 scopus 로고
    • Prior to this work, Nelson reported the equilibration of a 2,2′-bifuranyl dimethyl acetal to the corresponding trans-fused pyrano[3,2-b]pyran in a beautiful synthesis of a ladder toxin intermediate see:
    • R. U. Lemieux A. A. Pavia J. C. Martin K. A. Watanabe Can. J. Chem. 1969 47 4427
    • (1969) Can. J. Chem. , vol.47 , pp. 4427
    • Lemieux, R.U.1    Pavia, A.A.2    Martin, J.C.3    Watanabe, K.A.4
  • 35
    • 0346668206 scopus 로고    scopus 로고
    • Warren has studied the equilibration of a 2,2′-bifuranyl with a cis-fused pyrano[3,2-b]pyran via intermediate epi-sulfonium ions see:
    • J. M. Holland M. Lewis A. Nelson J. Org. Chem. 2003 68 747
    • (2003) J. Org. Chem. , vol.68 , pp. 747
    • Holland, J.M.1    Lewis, M.2    Nelson, A.3
  • 39
    • 0033584884 scopus 로고    scopus 로고
    • 13C NMR which indicated that the anomeric iodides were in intermediate exchange on the NMR timescale; cooling the sample did not result in significant sharpening of the resonances
    • D. Craig M. W. Pennington P. Warner Tetrahedron 1999 55 13495
    • (1999) Tetrahedron , vol.55 , pp. 13495
    • Craig, D.1    Pennington, M.W.2    Warner, P.3
  • 49
    • 0000622597 scopus 로고    scopus 로고
    • We orginally attempted to methylenate the bis-δ-lactone 8 with dimethyl titanocene to give the corresponding bis-exo-cyclic enol ether which would under go allylic oxidation to give 6 directly. However, exposure of 8 to dimethyltitanocene delivered solely the bis-endo-cyclic enol ether 42 in variable yield; the use of the Tebbe reagent resulted in decomposition. Attempted allylic oxidation of the enol ether 42 with either stoichiometric or catalytic selenium dioxide was also unsuccessful
    • L. Alcaraz A. Cridland E. Kinchin Org. Lett. 2001 3 4051
    • (2001) Org. Lett. , vol.3 , pp. 4051
    • Alcaraz, L.1    Cridland, A.2    Kinchin, E.3
  • 68
    • 0039536685 scopus 로고
    • 2-symmetric pyrano[3,2-b]pyrans reported in this work (see ESI) Crystal structure determination: crystallographic data of sulfone 38 was collected on the synchrotron radiation source at Station 9.8, Daresbury SRS, UK, on a Bruker SMART CCD diffractometer. The structures were solved by direct methods using the program SIR92 (idrefs="cit65" position= "baseline" ref. 65).
    • L. Norskov R. B. Jensen G. Schroll Acta Chem., Scand. Ser. B: Org. Chem. Biochem. 1983 37 133
    • (1983) Acta Chem., Scand. Ser. B: Org. Chem. Biochem. , vol.37 , pp. 133
    • Norskov, L.1    Jensen, R.B.2    Schroll, G.3
  • 78
    • 0032568331 scopus 로고    scopus 로고
    • We attempted to convert the asymmetric diol 53b into the symmetric diol 53a by an oxidation, epimerisation, reduction sequence. Treatment of the mixture of diols 53 with Jones' reagent gave the corresponding separable diketones. Disappointingly, attempted epimerisation of the resulting diketones under basic conditions resulted in decomposition (see ESI)
    • D. A. Evans B. W. Trotter B. Cote Tetrahedron Lett. 1998 39 1709
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1709
    • Evans, D.A.1    Trotter, B.W.2    Cote, B.3
  • 81
    • 0001767418 scopus 로고
    • The acetal carbon in 58 is a chirotopic non-stereogenic centre according the classification of Mislow see:
    • S. L. Schreiber Z. Y. Wang G. Schulte Tetrahedron Lett. 1988 29 4085
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4085
    • Schreiber, S.L.1    Wang, Z.Y.2    Schulte, G.3
  • 97
    • 10644276204 scopus 로고
    • 13C NMR chemical shifts for the natural and synthetic material see the ESI Compounds 71 and 72 were formed as mixtures (and yields are for the mixture) along with their corresponding diastereomers arising from silylation of the diol 53b. The minor diastereomer was removed after chlorination to give 73 The reported conditions were particularly effective:
    • S. Hanessian J. M. Vatele Tetrahedron Lett. 1981 22 3579
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3579
    • Hanessian, S.1    Vatele, J.M.2
  • 100
    • 0003787433 scopus 로고    scopus 로고
    • D. H. R. Barton, O. Meth-Cohn, and K. Nakinishi, Elsevier, Oxford, p. 301
    • A. Murai, in Comprehensive Natural Products Chemistry, ed., D. H. R. Barton, O. Meth-Cohn, and, K. Nakinishi, Elsevier, Oxford, 1999, p. 301
    • (1999) Comprehensive Natural Products Chemistry, Ed.
    • Murai In, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.