Novel and practical asymmetric synthesis of an azetidine alkaloid, penaresidin B

Tetrahedron Letters

Volumn 44, Issue 5, 2003, Pages 977-979

  Yoda, Hidemi ^a   Uemura, Takuya ^a   Takabe, Kunihiko ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

Author keywords

Arabinofuranose; Azetidine alkaloid; Lactam; Nucleophilic addition; Penaresidin

Indexed keywords

ALKALOID DERIVATIVE; AZETIDINE DERIVATIVE; LACTAM; MYOSIN ADENOSINE TRIPHOSPHATASE; PENARESIDIN B; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; HYDROGENATION; LOW TEMPERATURE; OXIDATION; REDUCTION; RING OPENING; STEREOCHEMISTRY;

EID: 0037467821     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02743-0     Document Type: Article

References (19)

1. Kaufer J.M., Hakomori S. Handbook of Lipids Research, Sphingolipid Biochemistry Vol. 3. 1983;Plenum Press, New York.
2. Sweeley C.C. Vance D.E., Vance J.E. Biochemistry of Lipids and Membranes. 1985;Benjamin/Commings, Menlo Park, CA.
3. Kobayashi J., Ishibashi M. Heterocycles. 42:1996;943-970.
4. Kobayashi J., Cheng J.-f., Ishibashi M., Wälchli M.R., Yamamura S., Ohizumi Y. J. Chem. Soc., Perkin Trans. 1. 1991;1135-1137.
5. Takikawa H., Maeda T., Seki M., Koshino H., Mori K. J. Chem. Soc., Perkin Trans. 1. 1997;97-111.
6. Kobayashi J., Tsuda M., Cheng J.-f., Ishibashi M., Takikawa H., Mori K. Tetrahedron Lett. 37:1996;6775-6776.
7. Hiraki T., Yamagiwa Y., Kamikawa T. Tetrahedron Lett. 36:1995;4841-4844.
8. Takikawa H., Maeda T., Mori K. Tetrahedron Lett. 36:1995;7689-7692.
9. Alvi K.A., Jaspars M., Crews P. Bioorg. Med. Chem. Lett. 4:1994;2447-2450.
10. Yajima A., Takikawa H., Mori K. Liebigs Ann. 1996;1083-1089.
11. Penaresidin A: (a) Ref. 6; (b) Ref. 3; (c) Knapp, S.; Dong, Y. Tetrahedron Lett. 1997, 38, 3813-3816; (d) Liu, D.-G.; Lin, G.-Q. Tetrahedron Lett. 1999, 40, 337-340. Penaresidin B: (a) Ref. 3; (b) Yoda, H.; Oguchi, T.; Takabe, K. Tetrahedron Lett. 1997, 38, 3283-3284.
12. Penaresidin A: (a) Ref. 6; (b) Ref. 3; (c) Knapp, S.; Dong, Y. Tetrahedron Lett. 1997, 38, 3813-3816; (d) Liu, D.-G.; Lin, G.-Q. Tetrahedron Lett. 1999, 40, 337-340. Penaresidin B: (a) Ref. 3; (b) Yoda, H.; Oguchi, T.; Takabe, K. Tetrahedron Lett. 1997, 38, 3283-3284.
13. Penaresidin A: (a) Ref. 6; (b) Ref. 3; (c) Knapp, S.; Dong, Y. Tetrahedron Lett. 1997, 38, 3813-3816; (d) Liu, D.-G.; Lin, G.-Q. Tetrahedron Lett. 1999, 40, 337-340. Penaresidin B: (a) Ref. 3; (b) Yoda, H.; Oguchi, T.; Takabe, K. Tetrahedron Lett. 1997, 38, 3283-3284.
14. Mori K. Tetrahedron. 32:1976;1101-1106.
15. Brown C.A., Yamashita A. J. Am. Chem. Soc. 97:1975;891-892.
16. Abrams S.R. Can. J. Chem. 62:1984;1333-1334.
17. Lay L., Nicotra F., Paganini A., Pangrazio C., Panza L. Tetrahedron Lett. 34:1993;4555-4558.
18. Yoda H., Yamazaki H., Kawauchi M., Takabe K. Tetrahedron: Asymmetry. 6:1995;2669-2672.
19. 9d however, in our case the desired cyclized product 10 was obtained in good yield (50%, two steps) with no difficulty. These different results would be ascribed to the steric bulkiness of both hydroxyl- and amino-protecting groups.