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Optische Aktivität und absolute Konfiguration von 1,4‐Dihydroxytricyclo[6.4.0.0 4,9 ]dodecan‐7,10‐dion und ‐7‐on
Author(s) -
Jürgensen Micael,
Roßnagel Ingrid,
Musso Hans
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240718
Subject(s) - chemistry , diastereomer , absolute configuration , dodecane , enantiomer , raney nickel , stereochemistry , organic chemistry , catalysis
Optical Activity and Absolute Configuration of 1,4‐Dihydroxytricyclo[6.4.0.0 4,9 ]dodecane‐7,10‐dione and ‐7‐one (±)‐1,4‐Dihydroxytricyclo[6.4.0.0 4,9 ]dodecane‐7,10‐dione ( 1 ) has been resolved into the pure enantiomers through chromatographic separation of the diastereomeric dithioacetals 3A and 3B prepared with (‐)‐( 2R , 3R )‐2,3‐butanedithiol ( 2 ). The dithioacetals were converted into the acetals 4 , from which the monoketones 6 were obtained by Raney nickel desulfurization/deprotection. The absolute configuration of (1R,4S,8S,9S)‐(‐)‐ 6 is correlated with that of (1 R ,4 S ,8 S ,9 S )‐(‐)‐ 1 by means of Cotton effects and its chromatographic behavior on potato starch. Some interaction between the carbonyl groups in the diketone 1 is demonstrated by comparison of UV, CD, and PE spectra with those of the monoketone 6 .