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A Novel Access to Ionone‐Type Compounds: ( E )‐4‐oxo‐β‐ionone and ( E )Oxo‐β‐irone via metal‐catalyzed intramolecular reactions of α‐diazo ketones with furans
Author(s) -
Wenkert Ernest,
Decorzant René,
Näf Ferdinand
Publication year - 1989
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.19890720416
Subject(s) - chemistry , ionone , intramolecular force , catalysis , ring (chemistry) , stereochemistry , diazo , ketone , enone , medicinal chemistry , organic chemistry
( E )‐5‐Demethyl‐4‐oxo‐β‐ionone ( 2 ), (E)‐4‐oxo‐β‐ionone ( 3 ), ( E )‐4‐oxo‐β‐irone ( 4 ), and the five‐membered ring analogs 36 – 41 were synthesized by a novel, convergent route starting from 2‐methylfuran ( 1 ). A recently discovered, intramolecular reaction of 2‐(diazoacyl)furans, catalyzed by dirhodium tetraacetate, leading to dienediones served as key step, thereby testing its utility in natural‐product synthesis for the first time.