Cihangir TANYELİ, Hülya AKGÜL, Volkan GÜLBEYAZ, Ayhan S. DEMİR

The facile synthesis of cyclopentanoid antibiotic kjellmanianone

ISSN: 1300-0527
Yayın Aralığı: Yılda 6 Sayı
Yayıncı: TÜBİTAK

The synthesis of cyclopentanoid antibiotic Kjellmanianone is described in this study. The C-acylation of lithium enolates of 3-Methoxycyclopentenone by N-carbomethoxyimidazole or methylcyanoformate b-ketoester, which when oxidized with Mn(III) acetate produces kjellmanianone in good yield.

PDF

___

1. T. Takenchi, H. Chimura, M. Hamada, H. Umezawa, 0. Yoshioka, N. Oguchi, Y. Takahashi, Matsuda, J. Antibiot., 28, 737, (1975).
2. W. Steglich, Pure & Appl. Chem., 53, 1233, (1981).
3. N. Nakayama, Y. Fukuoka, H. Nozaki, A. Matsuo, S. Hayashi, Chem. Lett., 1243, (1980).
4. (a) H. 0. House, G. H. Rasmussen, J. Org. Chem., 28, 27 (1963). (b) M. Koreeda, Y. P. Liang, H. Akagi, J. Chem. Soc. Chem. Commun., 449, (1979). (c) M. L. Quesada, R. H. Schlessinger, W. H. Parsons, J. Org. Chem., 43, 3963, (1978).
5. (a) L. N. Mander, S. P. Sethi, Tetrahedron lett., 24, 5425, ( 1983). (b) M. A. Childs, W. P. Weber, J. Org. Chem., 41, 3486, (1976).
6. (a) D. Boschelli, III, A. B. Smith, 0. D. Stringer, R. H. Jenkins, F. A. Davis, Tetrahedron Lett., 22, 4385, (1991). (b) B. C. Chen, M. C. Weismiller, F. A. Davis, D. Boschelli, J. R. Empfield, A. B. Smith III, Tettrahedron., 47, 173, (1991).
7. H. Irle, J. Katakawa, M. Tomida, Y. Mizuno, Chem. Lett., 537, (1981).
8. (a) A. S. Demir, A. Jeganathan, D. S. Watt, J. Org. Chem., 54, 4020, (1989). (b) A. S. Demir, N. camkerten, H. Akgun, C. Tanyeli, A. S. Mahasneh, D. S. Watt, Synthetic Commun., 20, 2279, (1990). (c) A. S. Demir, T. Sayrac, D. S. Watt, Synthesis., 1119, (1990). (d) A. S. Demir, A. Jeganathan, (Review), Synthesis, 2, (1992). (e) A. S. Demir, H. Akgiin, Z. calislcan, E. ozgfil, Bull. Chem. Soc. Fr., 132, 423, (1995). (g) A. S. Demir, A. Saatcloglu, Synthetic. Comm., 23, 571, (1993).
9. E. J. Corey, C. P. Schaefer, J. Am. Chem. Soc., 82, 918, (1960).