Preparation and a novel rearrangement reaction of 1, 2, 3, 4-tetrahydro-9-hydroxy-β-carboline, and their applications for the total synthesis of (±)-coerulescine

Heterocycles

Volumn 53, Issue 1, 2000, Pages 7-10

  Somei, Masanori ^a   Noguchi, Koichi ^a   Yamagami, Ryutaro ^a   Kawada, Yumiko ^a   Yamada, Koji ^a   Yamada, Fumio ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOLINE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033960644     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-8743     Document Type: Article

References (16)

1. a) This is Part 95 of a series entitled "The Chemistry of Indoles".
2. b) Part 94: M. Hasegawa, K. Yamada, Y. Nagahama, and M. Somei, Heterocycles, 2000, submitted. All new compounds gave satisfactory spectral and elemental analysis or high-resolution MS data for crystals or gums, respectively, la, mp 171-ITS'C (decomp); le, mp 181-183t: (decomp); Id, gum; 2a, gum; 2c, mp 111-112°C; 5, mp 205.0-206.5°C; 6, mp 193.5-195.0°C (decomp); 7, mp 254.0-265.5 (decomp); 11, mp 179.5-181.0°C; ISa, mp 207-209°C (decomp); 15b, mp 194-195°C.
3. a) M. Somei, N. Oshikiri, M; Hasegawa, and F. Yamada, Heterocycles, 1999, 51, 1237;
4. b) Review; M. Somei, ibid., 1999, 50, 1157 and references cited therein.
5. a) Review; M Somei, J. Synth. Org. Chem. Jpn., 1991, 49, 205;
6. b) M Somei and M. Natsume, Tetrahedron Lett., 1973, 2451;
7. M. Somei and Y. Fukui, Heterocycles, 1993, 36, 1859. See also reference 2b.
8. a) N. Anderton, P. A Cockrum, S. M. Colegate, J. A Edgar, K. Flower, I. Vit, and R. I. Willing, Phytochemistry, 1998, 48, 437.
9. b) S-I. Bascop, J. Sapi, J-Y. Laronze, and J. Levy, Heterocycles, 1994, 38, 725.
10. M.E. Kuehne, D. M. Roland, and R. Hafter, J. Org. Chem., 1978, 43, 3705.
11. C. Pellegrini, C. Strassler, M. Weber, andH-J. Borschberg, Tetrahedron:Asymmetry, 1994, 5, 1979; G. Lakshmajah, T. Kawabata, M. Shang, and K. Fuji, J. Org. Chem., 1999, 64, 1699. See also reference 4b.
12. M. Somei, K. Kobayashi, K. Tanii, T. Mochizuki, Y. Kawada, and Y. Fukui, Heterocycles, 1995, 40, 119.
13. M. Somei and T. Kawasaki, Heterocycles, 1989, 29, 1251; M Somei, T. Kawasaki, K. Shimizu, Y. Fukui, andT. Ohta, Chem. Pharm. Bull., 1991, 39, 1905. See also references 2b and 8. Our synthetic method for 1-hydroxy- and 1-alkoxytryptophans has been utilized by chemists without citing us fairly. One recent example is the following. D. L. Boger, H. Keim, B. Oberhauser, E. P. Schreiner, and C. A. Foster, J. Am. Chem. Soc., 1999, 121, 6197.
14. M. Somei and T. Kobayashi, Heterocycles, 1992, 34, 1295.
15. Synthesis of 8 from 9 in 78% yield: M. Natsume and R. Tanabe, Ann. Rept. ITSUULab., 1968, 15, 21 and references cited therein.
16. Remarkable differences observed in the reactivities of la, c and Id might be explained by the protonation of β-nitrogen. The detailed elucidation of the results is an interesting future subject.