Use of a sulfinyl tether to control diastereofacial selectivity in [5C + 2C] pyrone-alkene cycloadditions

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5885-5886

  Rumbo, Antonio ^a   Castedo, Luis ^a   Mascareñas, José L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE;

EID: 0030760708     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01310-5     Document Type: Article

References (12)

1. Rumbo, A.; Castedo, L.; Mouriño, A.; Mascareñas, J. L. J. Org. Chem. 1993, 58, 5585.
2. For recent asymmetric approaches to 8-oxabicyclo[3.2.1]octane units, see: (a) Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774.
3. (b) Lautens, M.; Aspiotis, R.; Colucci, J. J. Am. Chem. Soc. 1996, 118, 10930.
4. Asymmetric temporary tethers have been used in other cycloaddition reactions, see : (a) Shea, K. J.; Gauthier, D. R. Jr. Tetrahedron Lett. 1994, 35, 7311.
5. (b) Craig, D.; Ford, M. J.; Stones, J. A. Tetrahedron Lett. 1996, 37, 535.
6. García Ruano, J. L.; Carretero, J. C.; Carreño, M. C.; Martín, L. M.; Urbano, A. Pure & Appl. Chem. 1996, 68, 925.
7. 3): 3, δ= 0.16 (s, 6H), 0.94 (s, 9H), 2.10 (ddd, J = 1.5, 8.2 and 14.4 Hz, 1H), 2.30 (ddd, J = 2.6, 8.2 and 14.0 Hz, 1H), 2.59 (dd, J = 11.8 and 13.4 Hz, 1H), 3.14 (dd, J = 1.3 and 15.3 Hz, 1H), 3.38 (dd, J = 7.0 and 13.4 Hz, 1H), 3.57 (d, J = 15.4 Hz, 1H), 3.74 (m, 1H, H-9), 4.78 (d, J = 8.3 Hz, 1H), 6.42 (s, 1H). 4: δ= 0.16 (s, 6H), 0.92 (s, 9H), 2.12 (ddd, J = 1.4, 8.0 and 13.7 Hz, 1H), 2.44 (ddd, J = 2.7, 8.3 and 14.2 Hz, 1H), 2.81 (m, 1H, H-9), 2.91 (t, J = 12 Hz, 1H), 3.41 (AB, J = 14.6 Hz, 2H), 3.77 (dd, J = 7.0 and 11.2 Hz, 1H), 4.85 (dd, J = 1.2 and 8.3 Hz, 1H), 6.19 (s, 1H).
8. Lett, R.; Marquet, A. Tetrahedron 1974, 30, 3379.
9. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem. Int. Ed. Eng.. 1994, 33, 1601 and references cited therein.
10. This compound was obtained by oxidation of the corresponding thioether, which was prepared as described previously (ref. 1).
11. (a) Parril, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319.
12. (b) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224.