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doi:10.1016/S0040-4039(00)83978-7 
Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.
Hideo Iida, *, Kiyoshi Fukuhara, Mitsuo Machiba and Toyohiko Kikuchi
Tokyo College of Pharmacy, 1432-1, Horinouchi, Hachioji, Tokyo 192-03 Japan
Available online 8 March 2001.
Abstract
(S)-3-amino-3-phenylpropionic acid, as an intermediate, was converted to dihydrocelacinnine and celabenzine.
References
S.M. Kupchan, H.P.J. Hintz, R.M. Smith, A. Karim, M.W. Cass, W.A. Cass, W.A. Court and M. Yatagai J. Chem. Soc. 329 (1974) Chem. Commun. .
S.M. Kupchan, H.P.J. Hintz, R.M. Smith, A. Karim, M.W. Cass, W.A. Court and M. Yatagai J. Org. Chem. 42 (1977), p. 3660. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (5)
H. Wagner and J. Burghart Hely. Chim. Acta 64 (1981), p. 283. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (4)
H. Wagner and J. Burghart Helv. Chim. Acta 65 (1982), p. 739. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (6)
J.S. McManis and B. Ganem J. Org. Chem. 45 (1981), p. 2041.
H. Yamamoto and K. Maruoka J. Am. Chem. Soc. 103 (1981), p. 6133. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (23)
H.H. Wasserman, R.P. Robinson and H. Matsuyama Tetrahedron Lett. 3493 (1980).
E. Fisher, H. Scheibler and R. Groh Chem. Ber. 43 (1910), p. 2070.
M. Furukawa, T. Okawara, Y. Noguchi and Y. Terawaki Chem. Pharm. Bull. 27 (1979), p. 2223. View Record in Scopus | Cited By in Scopus (20)
mp 130–132°C; [α]25D −42.2° (c=0.54 EtOH); IR (nujol): 3360, 1680cm−1; NMR (CDCl3): δ 1.4 (s, 9H), 2.85 (d, J=7Hz, 2H), 5.0 (m, 1H), 7.3 (s, aromatic-H)
IR (neat): 3350, 1700, 1620cm−1; NMR (CDCl3): δ 1.4 (s, 9H), 5.0 (m, 1H), 6.7–7.7 (m, aromatic-H); MS: m/e 657 (M+).
oil; [α]25D −15.0° (c=0.72 CHCl3); IR (neat): 3350, 1690, 1620cm−1; NMR (CDCl3): δ 1.4 (s, 9H), 5.0 (m, 1H), 6.7–7.7 (aromatic-H); MS: m/e 525 (M+).
oil; IR (neat): 3350, 1700, 1620cm−1; NMR (CDCl3); δ 1.4 (s, 9H), 5.0 (m, 1H), 6.8–7.4 (m, aromatic-H), 9.8 (s, 1H); MS: m/e 523 (M+).
mp 180–183°C; [α]25D −17.7° (c=0.23 CHCl3); CD (MeOH) 224, 261, 268, (Δ
−4.8, 0.23, 0.23); IR (nujol) 3330, 1630, 1560cm−1; NMR (CDCl3): δ 1.1–4.0 (m, 22H), 3.97 (t, J=7Hz, 1H), 2.50 (d, J=7Hz, 2H), 7.15–7.50 (m, aromatic-H); MS: m/e 407 (M+).
oil; [α]25D −10.5° (c=0.32 CHCl3); IR (neat): 3300–3400, 1720cm−1; NMR (CDCl3): δ 1.40 (s, 9H), 5.0 (m, 1H), 7.2–7.6 (m, aromatic-H), 7.9–8.1 (d---d, 2H); MS: m/e 601 (M+).
mp 108–110°C; [α]25D −13.2° (c=0.44 CHCl3); IR (nujol) 3330, 1670, 1640, 1620cm−1; NMR (CDCl3): δ 1.40 (s, 9H), 5.0 (m, 1H), 7.2–7.5 (m, aromatic-H), 7.8–8.0 (d---d, 2H); MS: m/e 497 (M+).
oil; IR (neat): 3350, 1710, 1700, 1650, 1610cm−, NMR (CDCl3): δ 1.40 (s, 9H), 5.0 (m, 1H), 7.1–7.5 (m, aromatic-H), 9.6 (s, 1H); MS: m/e 495 (M+).
mp 170–173°C; [α]25D ±0° (c=0.73 CHCl3); CD (MeOH) 233, 250, 262, 268 (Δ −2.9, 0.64, 0.47, 0.32): IR (nujol): 3300, 1660, 1610cm−1; NMR (CDCl3): δ 1.2–2.2 (m, 7H), 2.25–2.75 (m, 4H), 2.8–3.9 (m, 6H), 3.95 (m, 1H), 7.2–7.5 (m, aromatic-H, 10H); MS: m/e 379 (M+).
