Stereoselective approach to the BCD framework of richardianidins via intramolecular Reformatsky-type reaction promoted by diethylaluminum chloride

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 5057-5060

  Sánchez, Mar ^a   Bermejo, Francisco ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM CHLORIDE; DITERPENE; RICHARDIANIDIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; MOLECULAR INTERACTION; OXIDATION; PLANT LEAF; STEREOCHEMISTRY; SYNTHESIS; TRADITIONAL MEDICINE;

EID: 0343907707     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01104-0     Document Type: Article

References (13)

1. Mossa, J. S.; Cassady, J.M.; Kozlowski, J.F.; Zennie, T. M.; Antoun, M. D.; Pellechia M. G.; McKenzie, A. T.; Byrn S. R. Tetrahedron Lett., 1988, 29, 3627-3630.
2. Cassady, J. M.; Antoun, M. D.; Byrn, S. R.; Mc Kenzie, A. T.; Kozlowski, J. F.; Main, P. J. Org. Chem., 1985, 50, 916-918.
3. Von Dreele, R. B.; Pettit, G. R.; Ode, R. H.; Perdue, R. E.; White, J. D.; Manchand, P. S. J. Am. Chem. Soc., 1975, 97, 6236.
4. Mahunnah, R. L. A.; Mtotmwema, K., J. Econ. Tox. Bot., 1985, 7, 505.
5. Creger, P. L. , J Am. Chem. Soc.,1967, 89, 2500.
6. Bornack, W. K.; Bhagwat, S. S.; Ponton, J.; Helquist, P. J. Am. Chem. Soc., 1981, 103, 4647-4648.
7. AC= 5.4 Hz) as already reported for similar systems. For a review see: Heathcock, C. H. in "Asymmetric synthesis", Academic Press 1984. Morrison, J. D. Ed. Vol. #3, Chapter 2.
8. 3): 1.29 (s, 3H); 1.31 (s, 3H); 1.67 (t, J= 12 Hz, 1H); 1.81 (s, 3H); 1.89 (dd, J= 12 Hz, J= 6 Hz, 1H); 1.98 (d, J= 3 Hz, 3H); 2.71 (m, 1H); 3.47 (tq, J= 11 Hz, J= 3 Hz, 1H); 4.86 (d, J= 11 Hz, 1H); 6.40 (m, 1H); 7.35 (m, 1H); 7.41 (m, 1H) ppm.
9. Maruoka, K.; Hashimoto, S; Kitagawa, Y.; Hisashi, Y; Nozaki, H. J. Am. Chem. Soc., 1977, 99, 7707-7709.
10. The 1,3 interaction with the vinyl residue may be responsible for the interaction of the enolate with the carbonyl functionality from the β side in the transition state leading to the major product, 10d. (Formula Presented)
11. Tsuji, J.; Shimizu, I.; Yamamoto, K. Tetrahedron Lett., 1976, 34, 2975.
12. Treatment of 12a with either m-chloroperbenzoic acid or trifluoroperacetic acid led to complex mixtures of difficult resolution. Reaction with magnesium monoperoxyphthalate, urea-hydrogen peroxide (UHP) or permaleic acid led to the recovery of the starting material. Likewise, treatment of (formula presented) 12a with tert-butyl hydroperoxide under basic conditions also failed.
13. The formation of 13 may be easily rationalized in terms of the nucleophilic attack of the furan moiety on the activated carbonyl function followed by oxidative transformations.