ISSN:
0899-0042
Keywords:
aloe
;
feroxidin
;
absolute configuration
;
tetralins
;
helicity
;
Cotton effect
;
conformation
;
half-chair cyclohexene ring
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The configuration of carbon-8 in feroxidin (1) was proven to be (S) by chemical correlation with (S)-methylsuccinic acid. Previous demonstration that 6-hydroxy and 8-methyl groups are equatorial and pseudoaxial, respectively, in a half-chair conformation of the cyclohexene ring (relative configuration) allowed the absolute stereochemistry of the whole molecule to be established (Fig. 3). The CD spectrum of feroxidin represents the first experimental test confirming the applicability of Snatzke's helicity rules to tetralins m-disubstituted on the aromatic ring.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530030409
Permalink