ISSN:
0170-2041
Keywords:
(-)-Salandrin
;
Sterids
;
1,4-Benzodioxane
;
Circular dichroism
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Starting from cholesterol the three possible stereoisomeric 1,4-benzodioxanes 24, 31, 32 and a series of analogues with 2βH,3βH configuration (25-27, 29, 30) have been synthesized. The α band of the 1,4-benzodioxane chrompohore has been unequivocally identified in the CD spectra between 325-300 nm. For its Cotton effect the same helicity rule is valid as for homochirally analogous tetralins: the P/M helicity of the heteroring leads to a positive/negative CD within the α-band. The (2′R,3′R) configuration of 6 has been established by a comparison of its CD data with those of 39 and with the help of the above-mentioned helicity rule. This allows the assignement of the (2S,2′R,3′R) configuration of (-)-silandrin (3).
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101115
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