Synthesis and antitumor evaluation of octahydro-5-hydroxy-1,5-imino-3-benzazocin-4,7,10-triones

Heterocycles

Volumn 46, Issue 1, 1997, Pages 309-320

  Saito, Naoki ^a   Sakai, Haruyuki ^a   Takai, Erika ^a   Muranaka, Riho ^a   Itabashi, Michiko ^a   Kubo, Akinori ^a   Yazawa, Katsukiyo ^b   Mikami, Yuzuru ^b  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005776077     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s16     Document Type: Article

References (11)

1. T. Arai and A. Kubo, 'The Alkaloids,' Vol. 21, ed. by A. Brossi, Academic Press, Inc., New York, 1983, pp. 55-100;
2. R. H. Thomson, 'Naturally Occurring Quinones III,' Chapman and Hall, New York, 1987, pp. 633-666;
3. A. Kubo and N. Saito, 'Studies in Natural Products Chemistry,1 Vol. 10, ed. by Atta-ur-Rahman, Elsevier, Inc., Amsterdam, 1992, pp. 77-145.
4. N. Saito, Y. Ohira, and A. Kubo, Chem. Pharm. Bull., 1990, 38, 821;
5. N. Saito, Y. Ohira, N. Wada, and A. Kubo, Tetrahedron, 1990, 46, 7711.
6. N. Saito, Y. Obara, T. Aihara, S. Harada, Y. Shida, and A. Kubo, Tetrahedron, 1994, 50, 3915.
7. H. Kurihara and H. Mishima, Tetrahedron Lett., 1982, 23, 3639;
8. A. Kubo, N. Saito, H. Yamato, R. Yamauchi, K. Hiruma, and S. Inoue, Chem. Pharm. Bull., 1988, 36, 2607.
9. In our total synthesis of (±)-saframycin B, we found it best in terms of the product yield to employ partial demethylation with boron tribromide followed by oxidative demethylation procedure to convert the polymethoxyarene to a p-quinone system; A. Kubo, N. Saito, H. Yamato, K. Masubuchi, and M. Nakamura, J. Org. Chem., 1988, 53, 4295. However, treating 6 with boron tribromide in dichloromethane allowed only an unstable polymeric material to be obtained.
10. 4 at 0 °C for 2 h afforded the corresponding 10-nitro derivative in 80% yield; N. Saito, Y. Obara, M. Azumaya, and A. Kubo, Chem. Pharm. Bull., 1992, 40, 2620. Treatment of this compound with 10 equiv of nitrobenzene in THF at -78 °C in the presence of 5 equiv of s-BuLi provided the alcohol (7) in 11% yield.
11. Stereochemistry of the methoxyl group in 13 was assigned based upon the clear observation of nuclear Overhauser effect (NOE) between 6-OMe (δ 3.74) and 11-Me (δ 2.59).