Direct asymmetric entry into the cytotoxic 8,9-secokaurene diterpenoids. Total synthesis of (-)-O-methylshikoccin and (+)-O-(methylepoxy)shikoccin

Journal of the American Chemical Society

Volumn 118, Issue 47, 1996, Pages 11990-11991

  Paquette, Leo A ^a   Backhaus, Dirk ^a   Braun, Ralf ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; DITERPENOID; O METHYLEPOXYSHIKOCCIN; O METHYLSHIKOCCIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0029853622     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962799d     Document Type: Article

References (24)

1. (a) Fuji, K.; Xu, H.-J.; Tatsumi, H.; Imahori, H.; Ito, N.; Node, M.; Inaha, M. Chem. Pharm. Bull. 1991, 39, 685 and relevant references cited therein.
2. (b) Nagao, Y.; Ito, N.; Kohno, T.; Kuroda, H.; Fujita, E. Chem. Pharm. Bull. 1982, 30, 727.
3. (c) Fuji, K.; Node, M.; Ito, N.; Fujita, E.; Takada, S.; Unemi, N. Chem. Pharm. Bull. 1985, 33, 1038.
4. Fujita, T.; Takeda, Y.; Shingu, T.; Kido, M.; Taira, Z. J. Chem. Soc., Chem. Commun. 1982, 162.
5. Fujita, E.; Ito, N.; Uchida, I.; Fuji, K.; Taga, T.; Osaki, K. J. Chem. Soc., Chem. Commun. 1979, 806.
6. Takeda, Y.; Futatsuishi, Y.; Matsumoto, T.; Terada, H.; Otsuka, H. Phytochemistry 1994, 35, 1289.
7. Takeda, Y.; Fujita, T.; Ueno, A. Phytochemistry 1983, 22, 2531.
8. Takeda, Y.; Ichihara, T.; Fujita, Y.; Ueno, A. Chem. Pharm. Bull. 1989, 37, 1213.
9. (a) Node, M.: Ito, N.; Fuji, K.; Fujita, E. Chem. Pharm. Bull. 1982, 30, 2639.
10. (b) Node, M.; Ito, N.; Uchida, I.; Fujita, E.; Fuji, K. Chem. Pharm. Bull. 1985, 33, 1029.
11. (a) Ladouceur, G.; Paquette, L. A. Synthesis 1992, 185.
12. (b) Paquette, L. A.; Ladouceur, G. J. Org. Chem. 1989, 54, 4278.
13. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528.
14. +.
15. Prepared from β-bromoacetaldehyde dimethyl acetal by displacement with cyanide ion, acetal exchange with β-trimethylsilyl ethanol (TsOH, toluene, heat), and Dibal-H reduction.
16. Lisphutz, B. H.; Harvey, D. F. Synth. Commun. 1982, 12, 267.
17. Backhaus, D. Unpublished results. This information will be included in the full paper.
18. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
19. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
20. (a) Holy, N.; Fowler, R.; Burnett, E.; Lorenz, R. Tetrahedron 1979, 35, 613.
21. (b) Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G.; Wenkert, E. Synth. Commun. 1992, 22, 2305.
22. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
23. 13C NMR, and high-resolution mass spectra in complete accord with their assigned structures. Elemental analyses were also obtained in many cases.
24. 3 (δ 3.26) were erroneously claimed to appear at δ 3.34 and 3.18, respectively. The spectra graciously provided to us by the original authors immediately revealed the source of confusion to be typographical.