Control of Ring Junction Stereochemistry via Radical Cyclization

Journal of the American Chemical Society

Volumn 107, Issue 2, 1985, Pages 500-501

  Stork, Gilbert ^a   Kahn, Michael ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845378234     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00288a038     Document Type: Article

References (10)

1. Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741.
2. Stork, G. In “Current Trends in Organic Synthesis”; Nozaki, H., Ed.; Pergamon Press: Oxford, 1983; pp 359–371.
3. Stork, G. In “Selectivity—A Goal for Synthetic Efficiency”; Bartmann, W., Trost, B. M., Ed.; Verlag Chemie: Basel, 1984; pp 281–299.
4. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765.
5. Removable connection to an allyl alcohol via a silyl ether is conceptually very similar to our previously used mixed acetal connection but differs in that it introduces a one-rather than a two-carbon functional chain at the α-carbon of the allylic alcohol double bond, via the carbon-silicon cleavage method of ref 6. Experiments on the silyl ether connection, using (bromomethyl)dimethylchlorosilane with allylic alcohols, were carried out in 1983 by Dr. Pawel Fludzinski in our laboratory. For a recent illustration of the silyl variation of the acetal cyclization, see: Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298.
6. Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2120.
7. Stevens, R. V.; Chapman, K. T.; Waller, H. N. J. Org. Chem. 1980, 45, 2030.
8. Stork, G.; d'Angelo, J. J. Am. Chem. Soc. 1974, 96, 7114.
9. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1973, 38, 3244.
10. Micheli, R. A.; Hajos, Z. G.; Cohen, N.; Parrish, D. R.; Portland, L. A.; Sciamanna, W.; Scott, M. A.; Wehrli, P. A. J. Org. Chem. 1975, 40, 675.