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Absolute configuration of feroxidin: An experimental support to snatzke's helicity rules for tetralins
Author(s) -
Speranza Giovanna,
Manitto Paolo,
Pezzuto Donata,
Monti Diego
Publication year - 1991
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530030409
Subject(s) - chemistry , absolute configuration , helicity , cyclohexene , ring (chemistry) , stereochemistry , molecule , computational chemistry , organic chemistry , catalysis , physics , particle physics
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.