A Facile Route to a Sensitive Terpene Alcohol : Regio-unselective Metalation of alpha-Terpinene as Key Step
Schlosser, Manfred; Bosshardt, Herbert; Walde, Annelis; Stoehle, Manfred
1980

Abstract

Treatment of a-terpinene (I, R = H) with BuLi-KOCMe3 followed by FB(OMe)2 and then alk. H2O2 soln. gave 44% anthemol (I, R = OH). The metalation step of a-terpinene presumably gave 3 pentadiene-K species (II-IV), which reacted with D2O and ClSiMe3 to give I, V, or VI (R = D, SiMe3) resp. [on SciFinder (R)]

Details

Title A Facile Route to a Sensitive Terpene Alcohol : Regio-unselective Metalation of alpha-Terpinene as Key Step
Author(s) Schlosser, Manfred ; Bosshardt, Herbert ; Walde, Annelis ; Stoehle, Manfred
Published in Angewandte Chemie, International Edition
Volume 19
Pages 303
Date 1980
Keywords
Note CAN 93:71963 30-10 Terpenoids Inst. Chim. Organ.,Univ. Lausanne,Lausanne,Switz. Journal 0044-8249 written in German. 99-87-6P Role: SPN (Synthetic preparation), FORM (Formation, nonpreparative), PREP (Preparation) (formation of, in prepn. of anthemol from a-terpinene); 99-86-5 Role: RCT (Reactant), RACT (Reactant or reagent) (metalation of, in prepn. of anthemol); 73286-73-4P; 73286-74-5P; 73286-75-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 22539-72-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, from a-terpinene)
DOI https://doi.org/10.1002/anie.198003031
Laboratories LSCO
Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2006-03-03

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