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Identification and Synthesis of Elymniafuran, a New Monoterpene from the Butterfly Elymnias thryallis
Author(s) -
Schulz Stefan,
Steffensky Mirjam,
Roisin Yves
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960612
Subject(s) - chemistry , lepidoptera genitalia , acetal , enantiomer , monoterpene , butterfly , furan , stereochemistry , gas chromatography , organic chemistry , botany , chromatography , ecology , biology
The main constituent of the scent gland secretion of the tropical butterfly Elymnias thryallis (Lepidoptera: Satyridae) could be identified as ( S )‐2‐methyl‐1‐(4‐methyl‐2‐furyl)‐3‐buten‐2‐ol (elymniafuran, 3 ). It is accompanied by small amounts of ( E )‐ and ( Z )‐4‐methyl‐(2‐methyl‐1,3‐butadienyl)‐furan ( 4 ) as well as the spiro acetal 3,9‐dimethyl‐1,6‐dioxaspiro[4.5]dec‐3‐ene ( 10 ). The structural assignment of these new natural products as well as the synthesis and enantiomeric separation by chiral gas chromatography are described.