Efficient Generation of the 15S Configuration in Prostaglandin Synthesis. Attractive Interactions in Stereochemical Control of Carbonyl Reduction

Journal of the American Chemical Society

Volumn 94, Issue 24, 1972, Pages 8616-8618

  Corey, E J ^a   Becker, Konrad B ^a   Varma, Ravi K ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; KETONE; PROSTAGLANDIN;

ARTICLE; CHEMICAL MODEL; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ESTERS; KETONES; MODELS, CHEMICAL; OXIDATION-REDUCTION; PROSTAGLANDINS; STEREOISOMERISM;

EID: 0015528959     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00779a074     Document Type: Article

References (10)

1. See, for example: E. J. Corey, S. M. Albonico, U. Koelliker, T. K. Schaaf, and R. K. Varma, J. Amer. Chem. Soc., 93, 1491 (1971);
2. C. J. Sih, R. Price, R. Sood, R. G. Salomon, G. Peruzzotti, and M. Casey, J. Amer. Chem. Soc., 94, 3643 (1972);
3. E. J. Corey and T. Ravindranathan, J. Amer. Chem. Soc., 94, 4013 (1972);
4. E. J. Corey and P. L. Fuchs, J. Amer. Chem. Soc., 94, 4014 (1972);
5. J. Fried, J. C. Sih, C. H. Lin, and P. Dalven, J. Amer. Chem. Soc., 94, 4343 (1972);
6. R. Pappo and P. W. Collins, Tetrahedron Lett., 2627 (1972).
7. See K. Noack and R. N. Jones, Can. J. Chem., 39, 2225 (1961).
8. M. J. van Geldcrcn, Recl. Trav. Chim. Pays-Bas, 52, 969 (1933).
9. Cooling bath: n-pentanc–liquid nitrogen; see R. E. Rondeau, J. Chem. Eng. Data, 11, 124 (1966).
10. See H. C. Brown and S. Krishnamurthy, J. Amer. Chem. Soc., 94, 7159 (1972).