A Facile Route to a Sensitive Terpene Alcohol : Regio-unselective Metalation of alpha-Terpinene as Key Step

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)]


Published in:
Angewandte Chemie, International Edition, 19, 303
Year:
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)
Laboratories:




 Record created 2006-03-03, last modified 2018-12-03


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