ISSN:
0009-2940
Keywords:
Circular dichroism
;
Tricyclo[6.4.0.04,9]dodecane-7,10-dione and -7-one,1,4-dihydroxy-
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Optical Activity and Absolute Configuration of 1,4-Dihydroxytricyclo[6.4.0.04,9]dodecane-7,10-dione and -7-one(±)-1,4-Dihydroxytricyclo[6.4.0.04,9]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 (1R,4S,8S,9S)-(-)- 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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19911240718
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