메뉴 건너뛰기




Volumn 111, Issue 22, 1989, Pages 8421-8430

Total Synthesis of d,l-Methynolide. Medium-Ring Sulfides by Ylide Ring Expansion

Author keywords

[No Author keywords available]

Indexed keywords

METHYNOLIDE;

EID: 0024459718     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00204a015     Document Type: Article
Times cited : (30)

References (26)
  • 1
    • 0000323898 scopus 로고
    • (b) For the preliminary account of the methynolide synthesis, see: Vedejs, E.; Buchanan, R. A.; Conrad, P. C.; Meier, G. P.; Mullins, M. J.; Watanabe, Y. J. Am. Chem. Soc. 1987, 109, 5878
    • Vedejs, E. Acc. Chem. Res. 1984, 17, 358. (b) For the preliminary account of the methynolide synthesis, see: Vedejs, E.; Buchanan, R. A.; Conrad, P. C.; Meier, G. P.; Mullins, M. J.; Watanabe, Y. J. Am. Chem. Soc. 1987, 109, 5878.
    • (1984) Acc. Chem. Res. , vol.17 , pp. 358
    • Vedejs, E.1
  • 2
    • 0000588439 scopus 로고
    • (b) Vedejs, E.; Buchanan, R. A. J. Org. Chem. 1984, 49, 1840
    • Vedejs, E.; Powell, D. W. J. Am. Chem. Soc. 1982, 104, 2046. (b) Vedejs, E.; Buchanan, R. A. J. Org. Chem. 1984, 49, 1840.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 2046
    • Vedejs, E.1    Powell, D.W.2
  • 3
    • 0000662179 scopus 로고
    • (b) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185
    • Vedejs, E.; Hagen, J. P. J. Am. Chem. Soc. 1975, 97, 6878. (b) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 6878
    • Vedejs, E.1    Hagen, J.P.2
  • 4
    • 85022524163 scopus 로고
    • (b) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147. (c) Grieco, P. A.; Finkelhor, R. S. J. Org. Chem. 1973, 38, 2245. Grieco, P. A.; Boxler, D.; Hiroi, K. J. Org. Chem. 1973, 38, 2572
    • Baldwin, J. E.; Hackler, R. E.; Kelly, D. P. J. Chem. Soc., Chem. Commun. 1972, 1311. (b) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147. (c) Grieco, P. A.; Finkelhor, R. S. J. Org. Chem. 1973, 38, 2245. Grieco, P. A.; Boxler, D.; Hiroi, K. J. Org. Chem. 1973, 38, 2572.
    • (1972) J. Chem. Soc., Chem. Commun. , vol.1311
    • Baldwin, J.E.1    Hackler, R.E.2    Kelly, D.P.3
  • 5
    • 0020789928 scopus 로고
    • (b) Vedejs, E.; Dophin, J. M.; Gapinski, D. M.; Mastalerz, H. Current Trends in Organic Synthesis; Pergamon Press: New York, NY, 1983; p 221. (c) Vedejs, E.; Dent, W. H. III; Gapinski, D. M.; McClure, C. K. J. Am. Chem. Soc. 1987, 109, 5437
    • Vedejs, E.; Gapinski, D. M. J. Am. Chem. Soc. 1983, 105, 5058. (b) Vedejs, E.; Dophin, J. M.; Gapinski, D. M.; Mastalerz, H. Current Trends in Organic Synthesis; Pergamon Press: New York, NY, 1983; p 221. (c) Vedejs, E.; Dent, W. H. III; Gapinski, D. M.; McClure, C. K. J. Am. Chem. Soc. 1987, 109, 5437.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5058
    • Vedejs, E.1    Gapinski, D.M.2
  • 7
    • 0016849172 scopus 로고
    • (b) Inanaga, J.; Katsuki, T.; Takimoto, S.; Ouchida, S.; Inoue, K.; Nakano, A.; Okukado, N.; Yamaguchi, M. Chem. Lett. 1979, 1021. (c) Oikawa, Y.; Tanaka, T.; Yonemitsu, O. Tetrahedron Lett. 1986, 27, 3647
    • Masamune, S.; Kim, C. V.; Wilson, K. E.; Spessard, G. O.; Georghiou, P. E.; Bates, G. S. J. Am. Chem. Soc. 1975, 97, 3512. (b) Inanaga, J.; Katsuki, T.; Takimoto, S.; Ouchida, S.; Inoue, K.; Nakano, A.; Okukado, N.; Yamaguchi, M. Chem. Lett. 1979, 1021. (c) Oikawa, Y.; Tanaka, T.; Yonemitsu, O. Tetrahedron Lett. 1986, 27, 3647.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 3512
    • Masamune, S.1    Kim, C.V.2    Wilson, K.E.3    Spessard, G.O.4    Georghiou, P.E.5    Bates, G.S.6
  • 11
    • 0039165156 scopus 로고
    • (b) Fava, A.; Paolucci, C.; Pollicino, S.; Sandri, E. J. Am. Chem. Soc 1978, 43, 4826. (c) Fava, A.; Cere, V.; Paolucci, C.; Pollicino, S.; Sandri, E. J. Am. Chem. Soc 1981, 46, 3315
    • Fava, A.; Ceré, V.; Paolucci, C.; Pollicino, S.; Sandri, E. J. Org. Chem. 1979, 44, 4128. (b) Fava, A.; Paolucci, C.; Pollicino, S.; Sandri, E. J. Am. Chem. Soc 1978, 43, 4826. (c) Fava, A.; Cere, V.; Paolucci, C.; Pollicino, S.; Sandri, E. J. Am. Chem. Soc 1981, 46, 3315.
    • (1979) J. Org. Chem. , vol.44 , pp. 4128
    • Fava, A.1    Ceré, V.2    Paolucci, C.3    Pollicino, S.4    Sandri, E.5
  • 18
    • 0000822952 scopus 로고
    • For evidence of chelation by α-sulfur, see (b) Shimagaki, M.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. J. Am. Chem. Soc 1984, 25, 4779
    • For evidence of chelation by α-sulfur, see: (a) Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, J.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775. (b) Shimagaki, M.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. J. Am. Chem. Soc 1984, 25, 4779.
    • (1984) Tetrahedron Lett , vol.25 , pp. 4775
    • Shimagaki, M.1    Maeda, T.2    Matsuzaki, Y.3    Hori, J.4    Nakata, T.5    Oishi, T.6
  • 23
    • 85022487222 scopus 로고    scopus 로고
    • Kinetic selectivity was determined by NMR methods on the crude product obtained from rapid workup at 0 °C
    • Kinetic selectivity was determined by NMR methods on the crude product obtained from rapid workup at 0 °C.
  • 24
    • 85022518830 scopus 로고
    • Wittig, R.; Reiff, H. Angew. Chem., Int. Ed. Engl. 1968, 7, 7
    • Wittig, G. Top. Curr. Chem. 1976, 67, 1. Wittig, R.; Reiff, H. Angew. Chem., Int. Ed. Engl. 1968, 7, 7.
    • (1976) Top. Curr. Chem. , vol.67 , pp. 1
    • Wittig, G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.