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Volumn 67, Issue 51, 2011, Pages 10045-10052

Biomimetic syntheses of ineleganolide and sinulochmodin C from 5-episinuleptolide via sequences of transannular Michael reactions

Author keywords

Biomimetic synthesis; Ineleganolide; Norcembranoid; Sinulochmodin C; Transannular cyclisation

Indexed keywords

5 EPISINULEPTOLIDE; CEMBRANOID; HORIOLIDE; INELEGANOLIDE; LITHIUM; MACROCYCLIC COMPOUND; SCABROLIDE A; SCABROLIDE B; SINULOCHMODIN C; UNCLASSIFIED DRUG;

EID: 81255208512     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.040     Document Type: Article
Times cited : (39)

References (26)
  • 1
    • 0033551744 scopus 로고    scopus 로고
    • The structure drawn in this paper for ineleganolide is misleading and indicates that the configuration at C5 is opposite to that established by the crystal structure
    • C.-Y. Duh, S.-K. Wang, M.-C. Chia, and M.Y. Chiang Tetrahedron Lett. 40 1999 6033 6035 The structure drawn in this paper for ineleganolide is misleading and indicates that the configuration at C5 is opposite to that established by the crystal structure
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6033-6035
    • Duh, C.-Y.1    Wang, S.-K.2    Chia, M.-C.3    Chiang, M.Y.4
  • 3
    • 0042382984 scopus 로고    scopus 로고
    • Ineleganolide has also been isolated from Sinularia leptoclados and S. parva; see
    • Ineleganolide has also been isolated from Sinularia leptoclados and S. parva; see A.F. Ahmed, R.-T. Shiue, G.-H. Wang, C.-F. Dai, Y.-H. Kuo, and J.-H. Sheu Tetrahedron 59 2003 7337 7344
    • (2003) Tetrahedron , vol.59 , pp. 7337-7344
    • Ahmed, A.F.1    Shiue, R.-T.2    Wang, G.-H.3    Dai, C.-F.4    Kuo, Y.-H.5    Sheu, J.-H.6
  • 9
    • 19944398808 scopus 로고    scopus 로고
    • For a review, which includes the pharmacological significance of cembranoids from the soft coral genus Sinularia, see
    • For a review, which includes the pharmacological significance of cembranoids from the soft coral genus Sinularia, see: H.N. Kamel, and M. Slattery Pharm. Biol. 43 2005 253 269
    • (2005) Pharm. Biol. , vol.43 , pp. 253-269
    • Kamel, H.N.1    Slattery, M.2
  • 12
    • 0842285254 scopus 로고    scopus 로고
    • For other synthetic studies towards rameswaralide, see
    • For other synthetic studies towards rameswaralide, see: A. Srikrishna, and D.H. Dethe Org. Lett. 6 2004 165 168
    • (2004) Org. Lett. , vol.6 , pp. 165-168
    • Srikrishna, A.1    Dethe, D.H.2
  • 21
    • 34547503508 scopus 로고    scopus 로고
    • Both the Z- and E-isomers of deoxypukalide 9 have recently been found in the octocoral Leptogorgia sp., see
    • Both the Z- and E-isomers of deoxypukalide 9 have recently been found in the octocoral Leptogorgia sp., see E. Dorta, A.R. Diáz-Marrero, I. Brito, M. Cueto, L. D'Croz, and J. Darias Tetrahedron 63 2007 9057 9062
    • (2007) Tetrahedron , vol.63 , pp. 9057-9062
    • Dorta, E.1    Diáz-Marrero, A.R.2    Brito, I.3    Cueto, M.4    D'Croz, L.5    Darias, J.6
  • 22
    • 79251495416 scopus 로고    scopus 로고
    • For further discussion see
    • For further discussion see: Y. Li, and G. Pattenden Nat. Prod. Rep. 28 2011 429 440
    • (2011) Nat. Prod. Rep. , vol.28 , pp. 429-440
    • Li, Y.1    Pattenden, G.2
  • 23
    • 11844249346 scopus 로고    scopus 로고
    • The β-epoxide corresponding to 12 and its C5 epimer, together with C13-oxy substituted metabolites corresponding to 12 and 13 have been reported in Sinularia sp. See Ref. 2 and also
    • The β-epoxide corresponding to 12 and its C5 epimer, together with C13-oxy substituted metabolites corresponding to 12 and 13 have been reported in Sinularia sp. See Ref. 2 and also A.F. Ahmed, J.-H. Su, Y.-H. Kuo, and J.-H. Sheu J. Nat. Prod. 67 2004 2079 2082
    • (2004) J. Nat. Prod. , vol.67 , pp. 2079-2082
    • Ahmed, A.F.1    Su, J.-H.2    Kuo, Y.-H.3    Sheu, J.-H.4
  • 26
    • 0001362991 scopus 로고
    • Beckwith et al. have calculated that the captodative carbon radical centre at C2 in 3(2H)-furanone itself is more stable than the corresponding carbon radical centre at C4 by 7.03 kcal/mol (relative to the C-H bond in n-propane). See
    • Beckwith et al. have calculated that the captodative carbon radical centre at C2 in 3(2H)-furanone itself is more stable than the corresponding carbon radical centre at C4 by 7.03 kcal/mol (relative to the C-H bond in n-propane). See: A.L.J. Beckwith, and A.A. Zavitsas J. Am. Chem. Soc. 117 1995 607 614
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 607-614
    • Beckwith, A.L.J.1    Zavitsas, A.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.