Facile synthesis of allixin and its related compounds

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2339-2340

  Matsumura, Yoshihiro ^a   Shirai, Kimihiro ^a   Maki, Toshihide ^a   Itakura, Yoichi ^b   Kodera, Yukihiro ^b  

^a NAGASAKI UNIVERSITY   (Japan)

^b WAKUNAGA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLIXIN; FURFURAL;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG ISOLATION; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; GARLIC; OXIDATION;

EID: 0032537092     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00148-8     Document Type: Article

References (13)

1. 1. a) Kodera, Y.; Matsuura, H.; Yoshida, S.; Sumida, T.; Itakura, Y.; Fuwa, T.; Nishino, H. Chem. Pharm. Bull. 1989,37,1656-1658.
2. b) Nishino, H.; Kodera, Y.; Sumida, T.; Yoshida, S.; Matsuura, H.; Itakura, Y. Jpn. Kokai Tokkyo Koho JP 02,311,462 (1990) [Chem. Abstr. 1991, 115, 35703b].
3. b) Nishino, H.; Kodera, Y.; Sumida, T.; Yoshida, S.; Matsuura, H.; Itakura, Y. Jpn. Kokai Tokkyo Koho JP 02,311,462 (1990) [Chem. Abstr. 1991, 115, 35703b].
4. 2. a) Nishino, H.; Nishino, A.; Iwashima, A.; Itakura, Y.; Kodera, Y.; Matsuura, H.; Fuwa, T. Cancer J. 1990, 3, 20-21.
5. b) Yamasaki, T.; Teel, R.W.; Lau, B.H.S. Cancer Lett. 1991, 59, 89-94.
6. c) Moriguchi, T.; Matsuura, H.; Itakura, Y.; Katsuki, H.; Saito, H.; Nishiyama, N. Life Sciences 1997, 61, 1413-1420, and references cited therein.
7. 3. Our method is based on a maltol synthesis exploited by one of authors: Shono, T.; Matsumura, Y. Tetrahedron Lett. 1976, 1363-1364.
8. 4. a) Fischer, E.; Oetker, R. Ber. 1913, 46, 4029-4040.
9. b) Nicolaou, K.C.; Hwang, C.-K.; Duggan, M.E. J. Am. Chem. Soc. 1989, 111, 6682-6690.
10. 5. Many unidentified products were formed.
11. 6. Arimoto, H.; Asano, S.; Uemura, D. Tetrahedron Lett. 1997, 38, 7761-7762.
12. 2; 9% yield.
13. 3): δ 0.95 (t, 3H, J=7.1Hz), 1.2-1.50 (m, 2H), 1.54-1.74 (m, 2H), 2.34 (s, 3H), 2.67 (t, 2H, J=7.5Hz), 3.88 (s, 3H), 6.36 (bs, 1H).