✦ LIBER ✦

Homologues of p-Menthane Derivatives in Roman Camomile

✍ Scribed by Alan F. Thomas; Marina Schouwey; Jean-Claude Egger

Book ID: 102856596
Publisher: John Wiley and Sons
Year: 1981
Tongue: German
Weight: 530 KB
Volume: 64
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19810640524

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✦ Synopsis

Abstract

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.

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