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Homologues of p ‐Menthane Derivatives in Roman Camomile
Author(s) -
Thomas Alan F.,
Schouwey Marina,
Egger JeanClaude
Publication year - 1981
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.19810640524
Subject(s) - chemistry , isopropyl , ketone , cyclohexane , stereochemistry , hydride , organic chemistry , metal
5‐Isopropyl‐2‐propyl‐2‐cyclohexen‐1‐one ( 1 ) and 5‐isopropyl‐2‐(2‐methylpropyl)‐2‐cyclohexen‐1‐one ( 2 ), homologues of the p ‐methene ketone carvotanacetone, have been identified in the oil of Anthemis nobilis . Their synthesis involved allylation of a cyclohexane‐1,3‐dione, and the acid‐catalyzed cyclization to dihydrofurans of the 2‐allylcyclohexane‐1,3‐diones is described. The stereochemistry of metal hydride reduction of 3‐ethoxy‐5‐isopropyl‐2‐propyl‐2‐cyclohexen‐1‐one ( 18 ) is mentioned in the course of the synthesis of the natural products. Some biogenetic considerations are discussed.