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Extra resources for Analytical Profiles of Drug Substances, Vol. 13
3 o i s s i e r , Y. Dunas, C. Advenier, Compt. Rend. SOC. B i o l . , 232 (1973)3. L. Hansson, H. Aberg, S. Jameson, Karlberg 549 (1973). R. Malmcrona, Acta Pled. Scand. 4. A. Amery, L. B i l l i e t , R. k g l . J. Ned, 2 o 284 (1974). 5. &8aplar, 2. hunC H. Eofman, J. Kuftinec, PI. Bkreblin, F. Kajfez, A. ITa I, IT. Blazev i 6 , Acta Pharm. , 2 ( 2 ) , 1983) i n press, 6. EfidBreitmaier, 'iJ. Jeinheim, 1978. 2 7. E. F'Jarmo, Drugs Bcptl. Clin. Ses. 6 , 639 (1980). 8. %. F. Poole, J. -Zlatkis, J.
1; Z = 2. This work has unambiguously d e f i n e d t h e a b s o l u t e s t e r e o c h e m i s t r y of (+)-3bromo camphor and hence t h e (+)-camphor. The l a t t e r may be r e p r e s e n t e d as [l] w i t h t h e gem-dimethyl b r i d g e below t h e plane. The s u b s t i t u t i o n of bromine a t (C-3) i n (+)-camphor g i v e s r i s e t o a t h i r d asym& t r i c c e n t r e . The [lOO]-projection of t h e s t r u c t u r e i n F i g . 1 shows t h a t bromine i s trans t o t h e gem-dimethyl b r i d g e ( e n d o - c o n f i g u r a t i o n ) as it i s i n t h e (+)-3bromo ca1nphor-9-~-sulphonate anion [ 2 ] ( 1 9 ) and i n bromoisofenchone ( 2 0 ) .
The s u b s t i t u t i o n of bromine a t (C-3) i n (+)-camphor g i v e s r i s e t o a t h i r d asym& t r i c c e n t r e . The [lOO]-projection of t h e s t r u c t u r e i n F i g . 1 shows t h a t bromine i s trans t o t h e gem-dimethyl b r i d g e ( e n d o - c o n f i g u r a t i o n ) as it i s i n t h e (+)-3bromo ca1nphor-9-~-sulphonate anion [ 2 ] ( 1 9 ) and i n bromoisofenchone ( 2 0 ) . This c o n t r a s t s w i t h t h e cis- 33 CAMPHOR L 4c & L Fig. 1. a-axis . A view of t h e s t r u c t u r e down t h e JABER S .