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Volumn 5, Issue 9, 2003, Pages 1543-1546

Total synthesis of the reputed structure of alcyonin and reassignment of its structure

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALCYONIN; DITERPENE; EPOXIDE; ESTER DERIVATIVE; HYDROXYL GROUP; PEROXIDE; UNCLASSIFIED DRUG; ALLYL COMPOUND; CARBON; ESTER; ETHER DERIVATIVE;

EID: 0038332053     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034384k     Document Type: Article
Times cited : (33)

References (33)
  • 2
    • 0036727043 scopus 로고    scopus 로고
    • For recent reviews of cladiellin, briarellin, and asbestinin diterpenes, see: (a) Sung, P.-J.; Chen, M.-C. Heterocycles 2002, 57, 1705-1715. (b) Bernardelli, P.; Paquette, L. A. Heterocycles 1998, 49, 531-556.
    • (2002) Heterocycles , vol.57 , pp. 1705-1715
    • Sung, P.-J.1    Chen, M.-C.2
  • 3
    • 0032585375 scopus 로고    scopus 로고
    • For recent reviews of cladiellin, briarellin, and asbestinin diterpenes, see: (a) Sung, P.-J.; Chen, M.-C. Heterocycles 2002, 57, 1705-1715. (b) Bernardelli, P.; Paquette, L. A. Heterocycles 1998, 49, 531-556.
    • (1998) Heterocycles , vol.49 , pp. 531-556
    • Bernardelli, P.1    Paquette, L.A.2
  • 14
    • 0141826101 scopus 로고    scopus 로고
    • note
    • The crude product 7 from the epoxy ester rearrangement-hydrolysis sequence was an inconsequential mixture of primary and secondary acetates.
  • 20
    • 0037486826 scopus 로고    scopus 로고
    • For a recent review, see: Fürstner, A. Chem. Rev. 1999, 99, 991-1045.
    • (1999) Chem. Rev. , vol.99 , pp. 991-1045
    • Fürstner, A.1
  • 21
    • 0001403350 scopus 로고
    • (a) Cladiellisin: δ 4.40 (H6), δ 72.6 (C6; 72.9 is reported in ref 19): Liu, J.; Zeng, L.; Wu, D. Chin. Sci. Bull. 1992, 37, 1627-1630.
    • (1992) Chin. Sci. Bull. , vol.37 , pp. 1627-1630
    • Liu, J.1    Zeng, L.2    Wu, D.3
  • 25
    • 0141714692 scopus 로고    scopus 로고
    • note
    • 1H NMR data for 6-epi-3 also were different from those reported for alcyonin.
  • 26
    • 0141491471 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra of natural alcyonin.
  • 28
    • 0141603070 scopus 로고    scopus 로고
    • note
    • 4.
  • 29
    • 33748817756 scopus 로고
    • Patai, S., Ed.; Wiley: New York
    • FAB or electrospray ionization, two methods not widely used in 1988, are often required to see the molecular ion of a hydroperoxide, see: (a) Schwarz, H.; Schiebel, H. M. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: New York, 1983; p 279. (b) Yu-Feng, H.; Wang, R.; Liu, Y.; Chang, Y.; Wang, Y.; Xia, C.; Suo, J. J. Mol. Catal. A: Chem. 2000, 159, 109-113.
    • (1983) The Chemistry of Peroxides , pp. 279
    • Schwarz, H.1    Schiebel, H.M.2
  • 30
    • 0034703484 scopus 로고    scopus 로고
    • FAB or electrospray ionization, two methods not widely used in 1988, are often required to see the molecular ion of a hydroperoxide, see: (a) Schwarz, H.; Schiebel, H. M. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: New York, 1983; p 279. (b) Yu-Feng, H.; Wang, R.; Liu, Y.; Chang, Y.; Wang, Y.; Xia, C.; Suo, J. J. Mol. Catal. A: Chem. 2000, 159, 109-113.
    • (2000) J. Mol. Catal. A: Chem. , vol.159 , pp. 109-113
    • Yu-Feng, H.1    Wang, R.2    Liu, Y.3    Chang, Y.4    Wang, Y.5    Xia, C.6    Suo, J.7
  • 31
    • 0028061725 scopus 로고    scopus 로고
    • See, inter alia: (a) Miyamoto, T.; Yamada, K.; Ikeda, N.; Komori, T.; Higuchi, R. J. Nat. Prod. 1994, 57, 1212-1219. (b) Ochi, M.; Yamada, K.; Futatsugi, K.; Kotsuki, H.; Shibata, K. Heterocycles 1991, 32, 29-32. (c) In our hands, 3 was readily acetylated.
    • (1994) J. Nat. Prod. , vol.57 , pp. 1212-1219
    • Miyamoto, T.1    Yamada, K.2    Ikeda, N.3    Komori, T.4    Higuchi, R.5
  • 32
    • 0003076139 scopus 로고
    • See, inter alia: (a) Miyamoto, T.; Yamada, K.; Ikeda, N.; Komori, T.; Higuchi, R. J. Nat. Prod. 1994, 57, 1212-1219. (b) Ochi, M.; Yamada, K.; Futatsugi, K.; Kotsuki, H.; Shibata, K. Heterocycles 1991, 32, 29-32. (c) In our hands, 3 was readily acetylated.
    • (1991) Heterocycles , vol.32 , pp. 29-32
    • Ochi, M.1    Yamada, K.2    Futatsugi, K.3    Kotsuki, H.4    Shibata, K.5
  • 33
    • 0028061725 scopus 로고    scopus 로고
    • note
    • See, inter alia: (a) Miyamoto, T.; Yamada, K.; Ikeda, N.; Komori, T.; Higuchi, R. J. Nat. Prod. 1994, 57, 1212-1219. (b) Ochi, M.; Yamada, K.; Futatsugi, K.; Kotsuki, H.; Shibata, K. Heterocycles 1991, 32, 29-32. (c) In our hands, 3 was readily acetylated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.