Total synthesis of (-)-(3R,6S,9R)-decarestrictine C2

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1199-1203

  Arai, Mayumi ^a   Morita, Nobuyasu ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Aldol reactions; Lactonization; Medium ring heterocycles; X ray crystal structures

Indexed keywords

DECARESTRICTINE C; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0034685301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02138-3     Document Type: Article

References (23)

1. (a) Grabley, S.; Granzer, E.; Hütter, K.; Ludwig, D.; Mayer, M.; Thiericke, R.; Till, G.; Wink, J.; Philipps, S.; Zeeck, A. J. Antibiot. 1992, 45, 56.
2. (b) Göhrt, A.; Zeeck, A.; Hütter, K.; Kirsch, R.; Kluge, H.; Thiericke, R. J. Antibiot. 1992, 45, 66.
3. Grabley, S.; Hammann, P.; Hütter, K.; Kirsch, R.; Kluge, H.; Thiericke, R.; Mayer, M.; Zeeck, A. J. Antibiot. 1992, 45, 1176.
4. (a) Andrus, M. B.; Shih, T.-L. J. Org. Chem. 1996, 61, 8780.
5. (b) Pilli, R. A.; Victor, M. M. Tetrahedron Lett. 1998, 39, 4421.
6. Yamada, S.; Tanaka, A.; Oritani, T. Biosci. Biotech. Biochem. 1995, 59, 1657.
7. (a) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739.
8. (b) Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381.
9. (c) Nokami, J.; Taniguchi, T.; Ogawa, Y. Chem. Lett. 1995, 43.
10. (d) Solladié, G.; Arce, E.; Bauder, C.; Carreño, M. C. J. Org. Chem. 1998, 63, 2332.
11. (a) Machinaga, N.; Kibayashi, C. J. Org. Chem. 1991, 56, 1386.
12. (b) Machinaga, N.; Kibayashi, C. Synthesis, 1992, 989.
13. (c) Machinaga, N.; Kibayashi, C. J. Org. Chem. 1992, 57, 5178.
14. (a) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1992, 34, 841.
15. (b) Noda, A.; Aoyagi, S.; Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 35, 841.
16. 2 as a catalyst as follows (unpublished result).
17. Saravanan, P.; Chandrasekhar, M.; Anand, R. V.; Singh, V. K. Tetrahedron Lett. 1998, 39, 3091.
18. Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391.
19. Nagao, Y.; Kumagai, T.; Nagase, Y.; Tamai, S.; Inoue, Y.; Shiro, M. J. Org. Chem. 1992, 57, 4232 and references cited therein.
20. Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Chem. Ind. (London) 1983, 643.
21. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
22. 3OD) δ 22.8, 29.9, 36.9, 48.0, 69.5, 74.6, 75.3, 132.2, 135.2, 173.4.
23. 2 (3/4) has been synthesized by the following sequence starting from (S,S)-8 via a nonstereoselective Reformatsky-type cyclization (Machinaga, N. PhD Thesis, Tokyo University of Pharmacy & Life Science, 1993).