The first total synthesis of floerkein B and barbi-lycopodin

Heterocycles

Volumn 46, Issue 1, 1997, Pages 123-127

  Kato, Nobuo ^a   Higo, Atsushi ^a   Wu, Xue ^b   Takeshita, Hitoshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b TOHWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001762353     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s44     Document Type: Article

References (25)

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16. N. Kato, H. Takeshita, S. Tanaka, and H. Kataoka, J. Chem. Soc., Perkin. Trans, 1, 1989, 1833 (1989).
17. Prolonged hydrolysis reaction of 14 caused epimerization of the aldehyde of the product (16) to form a thermodynamically stable hemiacetal (25). (Figure Presented)
18. A. Mori, K. Kinoshita, M. Oda, and S. Inoue, Chem. Lett., 1990, 1171.
19. 1H NMR evidences; in 17, methine and hydroxyl protons of the cyanohydrin moiety appeared at 4.47 and 6.19 ppm, respectively, both as broad singlets. This fact was only explainable with hydrogen bond between two hydroxyl groups and S-configuration of the cyanohydrin moiety in 17.
20. For the medium to large membered ring formation by the intramolecular alkylation using a carbanion generated from protected cyanohydrins, see, T. Takahashi, T. Nagashima, and J. Tsuji, Tetrahedron Lett., 1981, 22, 1359;
21. T. Takahashi, H. Ikeda, and J. Tsuji, Tetrahedron Lett., 1981, 22, 1363;
22. T. Takahashi, T. Doi, and H. Nemoto, J. Synth. Org. Chem., Jpn., 1989, 47, 135; and references cited therein.
23. Low-valent titanium salt mediated cyclization on a diformyl derivative to form the eleven-membered ring was also successful, but the presence of an extra oxygen function seems to be disadvantageous.
24. 3OD)=1.20, 1.26, 1.37, 1.39, and 1.43(each 3H, s), 2.94(1H, d, J=9 Hz), 3.10(1H, dd, J=10, 4 Hz), and 4.13(1H, ddd, J=12, 6, 2 Hz)].
25. 3OD)=1.29, 1.36, 1.42 1.48, 1.54, 1.99, and 2.06(each 3H, s), 2.87(1H, d, J=8 Hz), 3.04(1H, dd, J=9, 5 Hz), and 5.38 (1H, ddd, J=12, 6, 2 Hz)].