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Volumn 76, Issue 2, 2008, Pages 1069-1074

Stereoselective synthesis of maitotoxin GHI-ring system having a 1,2-diol side chain

Author keywords

Alkoxyacrylate; Alkoxyvinyl Sulfoxide; Cyclization; Samarium Diiodide; Tetrahydropyran

Indexed keywords


EID: 61349161187     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(N)113     Document Type: Article
Times cited : (4)

References (48)
  • 3
    • 1542502091 scopus 로고
    • For reviews on marine polycyclic ethers, see:
    • For reviews on marine polycyclic ethers, see:. Yasumoto T., and Murata M. Chem. Rev. 93 (1993) 1897
    • (1993) Chem. Rev. , vol.93 , pp. 1897
    • Yasumoto, T.1    Murata, M.2
  • 38
    • 61349171660 scopus 로고    scopus 로고
    • The yield was not optimized yet. The reaction was accompanied by decomposition
    • The yield was not optimized yet. The reaction was accompanied by decomposition.
  • 39
    • 0000136219 scopus 로고
    • For several examples of the synthesis of cyclic ethers via intramolecular herero-Michael reaction, see:
    • For several examples of the synthesis of cyclic ethers via intramolecular herero-Michael reaction, see:. Nicolaou K.C., Hwang C.-K., and Duggan M.E. J. Am. Chem. Soc. 111 (1989) 6682
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6682
    • Nicolaou, K.C.1    Hwang, C.-K.2    Duggan, M.E.3
  • 46
    • 61349171037 scopus 로고    scopus 로고
    • 16a
    • 16a
  • 47
    • 61349134546 scopus 로고    scopus 로고
    • Data for 17: IR (neat) 2926, 2855, 1749, 1455, 1373, 1218, 1097, 1057, 867, 742, 700, 602, 508 cm-1, 1H NMR (600 MHz, CDCl3) δ 7.53-7.28 (m, 8H, 7.21-7.19 (m, 2H, 5.56 (ddd, J, 7.9, 4.9, 2.6 Hz, 1H, 5.16 (d, J, 2.6 Hz, 1H, 4.62 (d, J, 12.5 Hz, 1H, 4.55 (d, J, 11.3 Hz, 2H, 4.49 (br dd, J, 4.2, 3.8 Hz, 1H, 4.40 (d, J, 11.3 Hz, 1H, 3.82 (dd, J, 9.3, 4.2 Hz, 1H, 3.75 (dd, J, 13.2, 11.0 Hz, 1H, 3.73 (s, 3H, 3.66 (dd, J, 11.0, 4.5 Hz, 1H, 3.56 (ddd, J, 11.3, 10.2, 4.4 Hz, 1H, 3.51 (ddd, J= 11.0, 10.3, 4.3 Hz, 1H, 3.41 (m, 1H, 3.32 (ddd, J= 9.6, 9.3, 2.5 Hz, 1H, 3.28 (dd, J, 9.1, 4.2 Hz, 1H, 3.16 (ddd, J= 11.0, 9.1, 4.2 Hz, 1H, 3.12 (ddd, J= 11.3, 9.1, 4.0 Hz, 1H, 2.57 (ddd, J, 11.3, 4.4, 4.0 Hz, 1H, 2.46 (ddd, J, 11.0, 4.3, 4.0 Hz, 1H, 2.19 (s, 3H, 2.06 (ddd, J, 14.3, 7.9, 2.5 Hz, 1H, 2.04 (s, 3H, 1.70 (ddd, J= 14.3, 9.6, 4.9 Hz, 1H, 1.64 (ddd, J= 11.3, 11.3, 11.3 Hz, 1H, 1.53 (s, 3H, 1.44 ddd, J, 11.0, 11.0
    • +) 735.2987, found 735.2958.
  • 48
    • 61349146006 scopus 로고    scopus 로고
    • 9 The present synthesis of the GHI-ring, including the construction of 1,2-diol side chain, was efficiently accomplished in 25 steps from 2-deoxy-D-ribose.
    • 9 The present synthesis of the GHI-ring, including the construction of 1,2-diol side chain, was efficiently accomplished in 25 steps from 2-deoxy-D-ribose.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.