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Isolation of a New Caryophyllane Ester from Lactarius subumbonatus : Conformational Analysis and Absolute Configuration
Author(s) -
Clericuzio Marco,
Toma Lucio,
Vidari Giovanni
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199909)1999:9<2059::aid-ejoc2059>3.0.co;2-h
Subject(s) - chemistry , absolute configuration , moiety , stereochemistry , sesquiterpene , circular dichroism , fatty acid , organic chemistry
(1 R ,6 R ,9 S )‐6‐Hydroxycaryophyllene ( S )‐6‐hydroxystearate, a sesquiterpene alcohol esterified by the unusual fatty acid ( S )‐(+)‐6‐hydroxystearic acid, has been isolated from the fruiting bodies of the Basidiomycete Lactarius subumbonatus . Both NMR data and AM1 calculations indicate that the caryophyllene macrocyclic ring adopts a ββ conformation. The absolute configuration of the sesquiterpene moiety has been established by theoretical Circular Dichroism calculations (De Voe coupled oscillators theory) and that of the fatty acid by NMR studies of the ( R )‐2‐methoxy‐2‐naphthylacetic acid (2‐NMA) ester.