By W. Klyne, John B. Buckingham
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1963,28,2381. W. H. De Camp and F. R. , 1972, B28, 1791. D. Fries and P. S. Portoghese,J. Medicin. Pharmaceut. 9hern. 1974,17,990. A. Gieren, P. Narayanan, W. Hoppe, M. Hasan, K. Michl, T. Wieland, H. O. Smith, G. Jung and E. Breitmaier, Annaien, 1974, 1561. G, Evrard, F. Durant and G. A. Dardenne, Cryst. Struct. , 1974,3,65. G. Hite and J. R. , 1973, B29, 2935. S. S. Ament, J. B. Wetherington, J. W. Moncrief, K. Flohr, M. Mochizuki and E. T. Kaiser, J. Amer. Chern. , 1973,95,7896. G. Hite and B_ M.
5 - bos (i- i£L. yl.. 2 -mefhy Ithllfon . _ . _ . _ . _ . _ . _ r ~ ' - ' - ' - ' - ' - ' -- i-- ' - '- ' - ' - ' - ' - ' - ' - ' - ' - '- ' C2 H , - y - Ph 10 . (S)-(-) 2_ i 7. (SH ) 3,3- (SH+)2-phenylfhilfon (CHz)zCOOH S. 4R) - ( )2,4-dihydroxy4 -corboxyhepfonedioic (phor b,c 1 ocid Class 2a, 3a Further cyclohexanes ' 15r COOMe 2 3 ....... '. :'HO"~' / ' ..... 2] ocl-5-ene-2,32,3-dlcarboxyllc acid, dlcarboxyllc aCid dlmelhyl esler I I I I 3. (iR, 2R)-(-) 1,2d,melhylcyclohexane \ cr AS(H) COOH " I " !
95, 105)- (+) decolln-I,5dlone ~ [/J 0 ~ [/J 5. (4S,9S, IOS)-(+)4-hydroxy-ldecolone. Ae by ORD [ / J Stereolsomers [ / J [/J c;p 8. [I] 9. (5S, 9S , lOS H+) 5-hydroxyI-decolone. AC by ORD [ / J o HWH COOH II. (IS,4R, 7R, 10R)- (-) frlqulnocene -2-corboxyI1c aCid [3J H 1[5J [3J o o 12. (IS, 4R, 7R, 10R)- (+) 2,3- 13. 0 4 , IO J t"cyclodecon -2dlhydrotnqUlnacen - 2- one By CD (,By-unsaturated ketone) [3J one. By CD (octant rule) [3J o 14. -5-hydrOxy-loctolone 1. P. Baumann and V. Prelog,Helv. Chim.