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A chemical study of burley tobacco flavour (nicotiana tabacumL.) VI. Identification and Synthesis of Four Irregular Terpenoids Related to Solanone, Including a ‘Prenylsolanone’

✍ Scribed by Edouard Demole; Paul Enggist

Book ID
102855518
Publisher
John Wiley and Sons
Year
1975
Tongue
German
Weight
758 KB
Volume
58
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Four novel constituents of Burley tobacco condensate have been identified as (E)‐5‐isopropyl‐7‐(2‐methyl‐tetrahydrofur‐2‐yl)‐hept‐6‐en‐2‐one (G), (E)‐5‐isopropyl‐7‐(2‐methyl‐tetrahydrofur‐2‐yl)‐hept‐6‐en‐2‐ol (H), (E)‐4‐methyl‐7‐isopropyl‐10‐oxo‐undec‐5‐en‐4‐olide (I), and (E, E)‐6,12‐dimethyl‐9‐isopropyltrideca‐5,10,12‐trien‐2‐one (J) or ‘prenylsolanone’. Compounds G, H, and I were synthesized from norsolanadione (1), compound J from solanone (A). These substances belong to a growing family of tobacco metabolites structurally related to solanone (A). Their possible formation from cembrene‐type precursors is briefly outlined.

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✍ Edouard Demole; Cécile Demole 📂 Article 📅 1975 🏛 John Wiley and Sons 🌐 German ⚖ 601 KB

## Abstract GLC. allowed the isolation of 1, 3, 6, 6‐tetramethyl‐5, 6, 7, 8‐tetrahydro‐isoquinolin‐8‐one (__A__) and 3,6,6‐trimethyl‐5,6‐dihydro‐__7H__‐2‐pyrindin‐7‐one (__D__) from __Burley__ tobacco condensate (about 0.1% each). The structures and syntheses of these novel terpenoid alkaloids are