First enantiocontrolled syntheses of (+)-uleine and
(+)-dasycarpidone
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Masanori Saito, Mitsuhiro Kawamura, Kou Hiroya and Kunio Ogasawara
Abstract
Stereocontrolled syntheses of (+)-uleine and (+)-dasycarpidone are
achieved for the first time in an enantiocontrolled way starting from
(+)-norcamphor.
References
J. E. Saxton, Nat. Prod. Rep., 1995, 12, 385 RSC and the former reports The Chemistry of Heterocyclic Compounds, ed.
J. E. Saxton,
Wiley-Interscience,
New York,
1983,
vol. 25, part 4, ch. 4; supplement to part 4,
1994 Search PubMed.
Racemic syntheses:
(a) A. Jackson, N. D. V. Wilson, A. J. Gaskell and J. A. Joule, J. Chem. Soc. C, 1969, 2738 RSC;
(b) L. J. Dolby and H. Biere, J. Org. Chem., 1970, 35, 3843 CrossRefCAS;
(c) T. Kametani and T. Suzuki, J. Org. Chem., 1971, 36, 1291 CrossRefCAS;
(d) J. Gracia, N. Casamitjana, J. Bonjoch and J. Bosch, J. Org. Chem., 1994, 59, 3939 CrossRefCAS;
(e) G. Büchi, S. J. Gould and F. Näf, J. Am. Chem. Soc., 1971, 93, 2492 CrossRef.
Utilization of (+)-norcamphor as a starting material for enantiocontrolled syntheses of natural products:
(a) M. Kawamura and K. Ogasawara, Tetrahedron Lett., 1995, 36, 3369 CrossRefCAS;
(b) M. Saito, M. Kawamura and K. Ogasawara, Tetrahedron Lett., 1995, 36, 9003 CrossRefCAS;
(c) M. Kawamura and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1995, 2403 RSC;
(d) M. Kawamura and K. Ogasawara, Heterocycles, 1997, 44, 129 CAS.
Cf. S. Takano and K. Ogasawara, J. Synth. Org. Chem. Jpn., 1977, 35, 795 Search PubMed; S. Takano, K. Hiroya and K. Ogasawara, Chem. Lett., 1983, 255 Search PubMed.
J. A. Marshall and D. E. Seitz, J. Org. Chem., 1974, 39, 1814 CrossRefCAS.
R. Bernardi and D. Ghiringhelli, J. Org. Chem., 1987, 52, 5021 CrossRefCAS; S. Müller, B. Liepold, G. J. Roth and H. J. Bestmann, Synlett, 1996, 521 CrossRef.
T. Tsunoda, M. Suzuki and R. Noyori, Tetrahedron Lett., 1980, 21, 1357 CrossRefCAS.
T. Sakamoto, Y. Kondo and H. Yamanaka, Heterocycles, 1986, 24, 31 CAS.
Utilization of this procedure for the natural product synthesis: S. Takano, T. Sato, K. Inomata and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1991, 402 Search PubMed; K. Shin and K. Ogasawara, Chem. Lett., 1995, 289 RSC; K. Shin and K. Ogasawara, Synlett, 1995, 859 CAS; K. Shin and K. Ogasawara, Synlett, 1996, 922 CrossRefCAS.
K. Sonogashira, Y. Tohda and N. Hagiwara, Tetrahedron Lett., 1975, 4467 CrossRefCAS.
N. Chidambaram and S. Chandrasekaran, J. Org. Chem., 1987, 52, 5048 CrossRefCAS.
J. A. Joule, M. Ohashi, B. Gilbert and C. Djerassi, Tetrahedron, 1965, 21, 1717 CrossRefCAS.
R. F. Garcia and K. S. Brown Jr., Phytochemistry, 1976, 15, 1093 CrossRef.
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