An enantio- and diastereocontrolled route to mintlactone and isomintlactone using a chiral cyclohexadienone equivalent

Synlett

Volumn , Issue 6, 1998, Pages 655-657

  Shimizu, Masahiro ^a   Kamikubo, Takashi ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003035374     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1747     Document Type: Article

References (26)

1. Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. Synthesis 1993, 948.
2. Hiroya, K.; Kurihara, Y.; Ogasawara, K. Angew. Chem. Int. Ed. Engl. 1995, 34, 2287.
3. Ogasawara, K. Pure & Appl. Chem. 1994, 66, 2119.
4. Recent examples, (a) A ring precursor of calcitriol: Kamikubo, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1995, 1951.
5. (b) (R)-Mevalonolactone: Shimizu, M.; Kamikubo, T.; Ogasawara, K. Tetrahedron: Asymmetry 1997, 8, 2519.
6. (c) (-)-Mesembrine and (+)-Sceletium Alkaloid A4: Kamikubo, T.; Ogasawara, K. Chem. Commun. in press.
7. (a) Fujita, S.; Fujita, Y. Nippon Nogeikagaku Kaishi, 1972, 46, 303.
8. (b) Sakata, I.; Hashizume, T. Agric. Biol. Chem. 1973, 37, 2441.
9. (c) Takahashi, K.; Someya, T.; Muraki, S.; Yoshida, T. Agric. Biol. Chem. 1980, 44, 1535.
10. Iwabuchi, H. 41st Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics, Morioka, Japan, Oct. 10-12, 1997, Abstract Paper pp. R1-R4.
11. Chiral syntheses of mintlactone 3 and isomintlactone 4: (a) Carda, M.; Marco, J. A. Tetrahedron Lett. 1991, 32, 5191.
12. (b) Carda, M.; Marco, J. A. Tetrahedron 1992, 48, 9789.
13. (c) Shishido, K.; Irie, O.; Shibuya, M. Tetrahedron Lett. 1992, 33, 4589.
14. (d) Crisp, G. T.; Meyer, A. G. Tetrahedron 1995, 51, 5831.
15. (e) Lohray, B. B.; Nandanan, E.; Bhushan, V. Indian J. Chem. 1997, 36B, 226.
16. Kozikowski, A. P.; Jung, S. H. J. Org. Chem. 1986, 51, 3402.
17. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1997, 765.
18. Tsuda, T.; Fujii, T.; Kawasaki, K.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1980, 1013.
19. Ashby, E. C.; Lin, J. J. Tetrahedron Lett. 1975, 44;
20. Ashby, E. C.; Lin, J. J.; Kovar, R. J. Org. Chem. 1976, 41, 1939.
21. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564.
22. Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554.
23. Grieco, P. A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett. 1978, 419.
24. Zipkin, R. E.; Natale, N. R.; Tafer, I. M.; Hutchins, R. O. Synthesis 1980, 3904.
25. Grieco, P. A.; Nishizawa, M.; Marinovic, N.; Ehmann, W. J. J. Am. Chem. Soc. 1976, 98, 7102.
26. 1H NMR, mass, high resolution mass) consistent with the assigned structure.