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Applications Synthétiques de la Cyclisation d′Alcools Tertiaires γ‐Éthyléniques en α‐Bromotétrahydrofurannes sous l'action du N‐Bromosuccinimide. III. Synthèse du Triméthyl‐2,6,10‐hydroxy‐10‐dodécatriène‐2,6,11‐al ( trans/trans et trans/cis ), Hydroxy‐Aldéhyde apparenté aux Sinensals
Author(s) -
Demole Edouard,
Enggist Paul
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560628
Subject(s) - chemistry , n bromosuccinimide , halogenation , medicinal chemistry , cis–trans isomerism , stereochemistry , organic chemistry
The reaction of 1‐formyl‐ethylidene‐triphenylphosphorane with trans ‐ and cis ‐4,8‐dimethyl‐8‐hydroxy‐deca‐4,9‐dienal ( 7 ) obtained from (±)‐nerolidol through a novel bromination/oxidation/debromination sequence, afforded 2,6,10‐trimethyl‐10‐hydroxy‐dodeca‐2,6‐11‐trienal 6 ( trans‐2/trans ‐6) and 10 ( trans‐2/cis ‐6), respectively. These hydroxyaldehydes closely related to the natural α‐ and β‐sinensals display a powerful, flower‐like odour.