Absolute configuration of feroxidin: An experimental support to snatzke's helicity rules for tetralins

✍ Scribed by Giovanna Speranza; Paolo Manitto; Donata Pezzuto; Diego Monti

• Book ID: 102076582
• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 449 KB
• Volume: 3
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.530030409

✦ Synopsis

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 rn-disubstituted on the aromatic ring.