Synthesis of a new versatile dienophile and its use in a highly diastereoselective Diels-Alder reaction

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 5015-5018

  Renaud, Jean Luc ^a   Aubert, Corinne ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Cyclisation; Diels Alder reactions; Gibberelins; Zinc

Indexed keywords

2 METHYENE 5 TRIMETHYLSILYL PENT 4 YN 1 OL; ALKADIENE; GIBBERELLIN; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; DRUG EFFECT; GROWTH REGULATION; PLANT GROWTH; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033516544     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00981-8     Document Type: Article

References (21)

1. (a) Fujita, E.; Node, N. Progress in the Chemistry of Organic Natural Products 1984, 46, 78.
2. (b) Phinney, B. O.; Spray, C. In Plant Growth Substances, Waring, P. F. Ed., Academic Press: London, 1982, 683.
3. Mander, L. N. Chem. Rev. 1992, 92, 573-612 and references cited therein.
4. (a) Cruciani, P.; Aubert, C.; Malacria, M. J. Org. Chem. 1995, 60, 2664-2665.
5. (b) Cruciani, P.; Stammler, R.; Aubert, C.; Malacria, M. J. Org. Chem. 1996, 61, 2699-2708.
6. (c) Cruciani, P.; Aubert, C.; Malacria, M. Synlett 1996, 105-107.
7. (a) Stammler, R.; Malacria, M. Synlett 1994, 92.
8. (b) Cruciani, P.; Aubert, C.; Malacria, M Tetrahedron Lett. 1994, 35, 6677-6680.
9. (c) Renaud, J. L.; Petit, M.; Aubert, C.; Malacria, M Synlett 1997, 931-932.
10. Mesnard, D.; Miginiac, L. J. Organomet. Chem. 1991, 420, 163-170.
11. Gaudemar, M. In Organometallic Syntheses, King, R. B; Eisch, J. J. Eds., Elsevier: Amsterdam, 1986, Vol. 3, 409.
12. Knoess, H. P.; Furlong, M. T.; Rozema, M. J.; Knochel, P. J. Org. Chem. 1991, 56, 5974-5978.
13. Mancuso, A. J.; Huang, S. L.; Swern, D. J. J. Org. Chem. 1978, 43, 2480-2482.
14. Danishefsky, S.; Kitahara, T.; Yan, C. F.; Morris, J. J. Am. Chem. Soc. 1979, 101, 6996-7000.
15. 11between the monoketal of glyoxal and the diethyl(acetyl)methylphosphonate. ii) a trapping of the enolate of the enone by tert-butyldimethylsilyl chloride.
16. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.;Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25,2183-2186.
17. (a) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166.
18. (b) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62,5252-5253.
19. (c) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039-3052.
20. 1,2 is 4.3 Hz means that the acetal and the propargyl group are in an unusual trans diaxial arrangement. In that favored conformation, we observed a NOE between the protons of the aldehyde and the acetal. (Formula presented)
21. A sample of the enynal 4 was given to the group of Dr. J. Rodriguez, University of Aix-Marseille III and it was also shown as a good Michael acceptor. See : Filipini, M. H. ; Rodriguez, J. J. Org. Chem. 1997, 62, 3034-3035.