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Structure and Synthesis of Novel C 12 Terpenoids from Quince Fruit ( Cydonia oblonga MILL.)
Author(s) -
Escher Sina,
Niclass Yvan
Publication year - 1991
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.19910740119
Subject(s) - chemistry , terpenoid , pulegone , stereochemistry , mill , terpene , organic chemistry , chromatography , essential oil
The structure and synthesis of novel irregular C 12 terpenoids isolated from quince fruit ( Cydonia oblonga MILL.) are described: quince oxepine (= ( E )‐2,3,6,7‐tetrahydro‐4‐methyl‐2‐(3‐methylbuta‐1,3 dienyl)oxepine; 3 ) and the quince oxepanes as a 1:1 mixture of cis ‐ and trans ‐isomers (= cis ‐ and trans ‐( E )‐4‐methyl‐2‐(3‐methylbuta‐1,3‐dienyl)oxepane; 4 and 5 , resp.). The absolute configurations of the natural compounds have not been determined due to the minute amounts available, but both relative and absolute configurations of synthetic 4 and 5 were established by chemial correlation with ( R )‐pulegone.