First enantioselective synthesis of manoalide: Application of aldehyde- dioxinone enantioselective condensation

Tetrahedron Asymmetry

Volumn 10, Issue 23, 1999, Pages 4481-4484

  Soriente, Annunziata ^a   De Rosa, Margherita ^a   Apicella, Aniello ^a   Scettri, Arrigo ^a   Sodano, Guido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; MANOALIDE; TITANIUM DERIVATIVE;

ACETYLATION; ALKYLATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033380296     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00529-7     Document Type: Article

References (21)

1. De Silva, E. D.; Scheuer, P. J. Tetrahedron Lett. 1980, 21, 1611.
2. For reviews, see: (a) Mayer, A. M. S.; Jacobs, R. S. In Biomedical Importance of Marine Organisms; Fautin, D. G., Ed.; California Academy of Sciences: San Francisco, 1988; pp. 133-142;
3. (b) Potts, B. C. M.; Faulkner, D. J.; Jacobs, R. S. J. Nat. Prod. 1992, 55, 1701;
4. (c) Mann, J. Nature 1992, 358, 540;
5. (d) Soriente, A.; De Rosa, M.; Scettri, A.; Sodano, G.; Terencio, M. C.; Paya, M.; Alcaraz, M. J. Curr. Med. Chem. 1999, 6, 415-431.
6. (a) Katsumura, S.; Fujiwara, S.; Isoe, S. Tetrahedron Lett. 1985, 26, 5827;
7. (b) Garst, M. E.; Tallman, E. A.; Bonfiglio, J. N.; Harcourt, D.; Ljungwe, E. B.; Tran, A. Tetrahedron Lett. 1986, 27, 4533;
8. (c) Katsumura, J.; Fujiwara, S.; Isoe, S. Tetrahedron Lett. 1988, 29, 1173;
9. (d) Bury, P.; Hareau, G.; Kocienski, P.; Dhanak, D. Tetrahedron 1994, 50, 8793;
10. (e) Pommier, A.; Kocienski, P. J. J. Chem. Soc., Chem. Commun. 1997, 1139;
11. (f) Coombs, J.; Lattmann, E.; Hoffmann, H. M. R. Synthesis 1998, 1367.
12. Ojima, I.; Kogure, T. Organometallics 1982, 1, 1390.
13. Soriente, A.; De Rosa, M.; Dovinola, P.; Sodano, G.; Scettri A. Tetrahedron: Asymmetry 1998, 9, 2197.
14. Sato, M.; Sunami, S.; Sugita, Y.; Kaneko, C. Heterocycles 1995, 41, 1435.
15. Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360.
16. Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
17. Shono, T.; Kashimura, S.; Sawamura, M.; Soejima, T. J. Org. Chem. 1988, 53, 907.
18. Chen, K. M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155.
19. Soriente, A.; De Rosa, M.; Scettri, A.; Sodano, G. Tetrahedron Lett. 1996, 37, 8007.
20. De Rosa, M.; Giordano, S.; Scettri, A.; Sodano, G.; Soriente, A.; Garcia Pastor, P.; Alcaraz, M. J.; Paya, M. J. Med. Chem. 1998, 41, 3232.
21. Kobayashi, M.; Okamoto, T.; Hayashi, K.; Yokoyama, N.; Sasaki, T.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 265.