107090-89-1Relevant articles and documents
Superacidic cyclization of ω-hydroxygeraniol diacetate and ω-hydroxygeraniol benzyl ether acetate
Kulcitki,Ungur,Deleanu,Vlad
, p. 136 - 138 (2007/10/03)
Low-temperature superacidic cyclization of (E,E)-3,7-dimethylocta-2,6-diene-1,8-diol (ω-hydroxygeraniol) diacetate and (E,E)-8-acetoxy-1-benzyloxy-3,7-dimethylocta-2,6-diene leads to the same mixtures of two diastereomeric 9-acetoxy-8-hydroxy-p-menth-1-enes epimeric at the C(8) atom.
Chemical Tranformation of Terpenoids. V. Acidic Conversions of 10-Hydroxygeraniol and 10-Hydroxynerol Derivatives Leading to Cyclic Monoterpenoids
Kitagawa, Isao,Tsujii, Shinji,Nishikawa, Fumiko,Shibuya, Hirotaka
, p. 2639 - 2651 (2007/10/02)
Acid treatment of 1-O-acetyl-10-hydroxygeraniol (5a), 1-O-methyl-10-hydroxygeraniol (5b), 1-O-acetyl-10-hydroxynerol (6a), and 1-O-methyl-10-hydroxynerol (6b) was investigated under various conditions.It was found that treatment of 5a and 6a with HCOOH gave menth-1-ene-8,9-diol (7), while treatment of 5a, 5b, 6a, or 6b with BF3-etherate in CH2Cl2 furnished two menthofuran-type compounds (9, 10) and two bicyclooct-2-ene derivatives (17, 24).Both 9 and 10 were successfully converted to menthofuran (16) and 17 was converted to a bicyclooctenone derivative (23) which was a key intermediate for a synthesis of juvabione (27).Keywords - geraniol; nerol; 10-hydroxygeraniol; 10-hydroxynerol; 10-hydroxygeraniol derivative; 10-hydroxynerol derivative; uroterpenol; menthofuran; bicyclooct-2-ene derivative