Mukaiyama-type, eight-membered ring closure: Access to a tricyclic system related to taxanes

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3133-3136

  Cavé, Christian ^a,b   Valancogne, Ingrid ^a   Casas, Ramon ^a   D'Angelo, Jean ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; ETHER DERIVATIVE; LITHIUM DERIVATIVE; TAXANE DERIVATIVE; TRICYCLIC AROMATIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; POLYMERIZATION; SYNTHESIS;

EID: 0032516297     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00461-4     Document Type: Article

References (19)

1. 1 EC Postdoctoral Fellow, on leave from the Universitat Autonoma de Barcelona (Spain).
2. 2 Taxol is a registered trademark for the substance also known under the generic name paclitaxel.
3. 3 For a relatively recent review, see: Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. For the most recent synthesis of Taxol, and references to others, see: Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; Mc Grane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757-2758.
4. 3 For a relatively recent review, see: Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. For the most recent synthesis of Taxol, and references to others, see: Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; Mc Grane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757-2758.
5. 4 For a recent eight-membered ring closure employing the protected cyanohydrin method, see: Stork, G.; Doi, T.; Liu, L. Tetrahedron Lett. 1997, 38, 7471-7474.
6. 5 Cavé, C. Boggero, S.; Casas, R.; Dumas, F.; Mahuteau, J.; d'Angelo, J. Tetrahedron: Asymmetry 1995, 6, 2647-2650.
7. 3) δ 4.4 (s, 1H), 3.95 (m, 2H), 2.10 (dd, J=7.1, 13.8 Hz, 1H), 2.0-1.4 (m, 4H), 1.1 (t, J=7.0 Hz, 3H), 0.95 ( s, 3H), 0.75 (s, 3H), 0.0 (s, 9H).
8. 3).
9. 2).
10. 9 Begbie, A. L.; Golding, B. T. J. Chem. Soc. Perkin I 1972, 602-605. When cyclization of diketone 9 was performed in the presence of MeONa in MeOH, the regioselectivity of the six-membered annulation was inverted.
11. 10 Ozonolysis of 10 was not chemoselective.
12. 3).
13. 3).
14. 13 Horiguchi,Y.; Furukawa, T.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 8277-8279.
15. 3).
16. 2CuLi was added to 13 at 0 °C, a double conjugate addition to the enone and enoate moieties was observed.
17. 3).
18. 3).
19. -1 than the corresponding trans-fused isomers by MM2 calculations.