Stereoselective total synthesis of cephalosporolide D

Heterocycles

Volumn 52, Issue 3, 2000, Pages 1105-1123

  Shiina, Isamu ^a   Fujisawa, Hidehiko ^a   Ishii, Toshihiro ^a   Fukuda, Yoshio ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CEPHALORIDE D; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034162585     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-S85     Document Type: Article

References (26)

1. M. J. Ackland, J. R. Hanson, P. B. Hitchcock, and A. H. Ratcliffe, J. Chem. Soc., Perkin Trans. 1, 1985, 843.
2. Isolation, a) D. M. Tapiolas, M. Roman, W. Fenical, T. J. Stout, and J. Clardy, J. Am. Chem. Soc., 1991, 113, 4682. Total synthesis.
3. b) K. R. Buszek, N. Sato, and Y. Jeong, J. Am. Chem. Soc., 1994, 116, 5511
4. c) J. C. McWilliams and J. Clardy, J. Am. Chem. Soc., 1994, 116, 8378.
5. Formal synthesis, d) K. R. Buszek and Y. Jeong, Tetrahedron Lett., 1995, 36, 7189
6. e) M. B. Andrus and A. B. Argade, Tetrahedron Lett., 1996, 37, 5049
7. f) M. Kodama, M. Matsushita, Y. Terada, A. Takuchi, S. Yoshio, and Y. Fukuyama, Chem. Lett., 1997, 117;
8. g) J. Bach and J. Garcia, Tetrahedron Lett., 1998, 39, 6761
9. h) S. Inoue, Y. Iwabuchi, H. Irie, and S. Hatakeyama, Synlett, 1998, 735.
10. Preliminary communication: I. Shiina, Y. Fukuda, T. Ishii, H. Fujisawa, and T. Mukaiyama, Chem. Lett., 1998, 831.
11. a) S. Kobayashi and T. Mukaiyama, Chem. Lett., 1989, 297
12. b) S. Kobayashi, H. Uchiro, I. Shiina, and T. Mukaiyama, Tetrahedron, 1993, 49, 1761;
13. c) S. Kobayashi, T. Kawasuji, and N. Mori, Chem. Lett., 1994, 217.
14. K. Ohta, O. Miyagawa, H. Tsutsui, and O. Mitsunobu, Bull. Chem. Soc. Jpn., 1993, 66, 523.
15. a) T. Mukaiyama, I. Shiina, and M. Miyashita, Chem. Lett., 1992, 625
16. b) M. Miyashita, I. Shiina, S. Miyoshi and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1993, 66, 1516
17. c) I. Shiina, S. Miyoshi, M. Miyashita, and T. Mukaiyama, Chem. Lett., 1994, 515
18. d) I. Shiina and T. Mukaiyama, Chem. Lett., 1994, 677
19. e) K. Ishihara, M. Kubota, H. Kurihara, and H. Yamamoto, J. Am. Chem. Soc., 1995, 117, 4413, 6639
20. f) K. Ishihara, M. Kubota, H. Kurihara, and H. Yamamoto, J. Org. Chem., 1996, 61, 4560.
21. Hafnium tetrakis(trifluoromethanesulfonate) was purchased from Tokyo Kasei Kogyo Co., Ltd. It was effectively employed in Friedel-Crafts reaction, Fries rearrangement and Mannich-type Reaction. See, I. Hachiya, M. Moriwaki, and S. Kobayashi, Bull. Chem. Soc. Jpn., 1995, 68, 2053;
22. S. Kobayashi, M. Moriwaki, and I. Hachiya, Bull. Chem. Soc. Jpn., 1997, 70, 267;
23. 4 and 2 mol eq. of AgOTf was effective catalyst for the synthesis of carboxylic esters in 1992. See, ref. 6a and 6b.
24. Buszek and Andrus suggested that conformations of the acyclic precursors for high-yielding lactonizations in the syntheses of octalactins are influenced by stereochemical arrangement and location of those protecting groups. See, ref. 2b and 2e.
25. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, and M. Yamaguchi, Bull. Chem. Soc. Jpn., 1979, 52, 1989.
26. T. Mukaiyama, M. Usui, and K. Saigo, Chem. Lett., 1976, 49.