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Epoxidation–cyclization of rosewood oxides
Author(s) -
Bombarda Isabelle,
Cezanne Lionel,
Gaydou Emile M.
Publication year - 2004
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.1311
Subject(s) - chemistry , traditional medicine , organic chemistry , medicine
The epoxidation reaction of linalool by MCPBA led to two furanoid oxides (35.7 and 37.0%), known as rosewood oxides, two pyranoid oxides (2.4 and 1.9%) and four rosewood epoxide derivatives. Reaction with BF 3 ‐MeOH of the epoxidized cis ‐furanoid oxide allowed the isolation of a new bicyclic compound [2‐(methoxymethyl)‐1,4,4‐trimethyl‐3,8‐dioxabicyclo(3.2.1)octane], whereas the epoxidized trans ‐furanoid oxide led to a new monocyclic diol methoxy ether [2‐(1‐hydroxy‐2‐methoxyethyl)‐5‐(1‐hydroxy‐1‐methylethyl)‐2‐methyltetrahydrofuran]. 2D‐NMR analyses were used for structure determination. Copyright © 2004 John Wiley & Sons, Ltd.