38049-04-6Relevant articles and documents
Regio- and stereoselective selenium dioxide allylic oxidation of (E)-dialkyl alkylidenesuccinates to (Z)-allylic alcohols: Synthesis of natural and unnatural butenolides
Patel, Ramesh M.,Puranik, Vedavati G.,Argade, Narshinha P.
, p. 6312 - 6322 (2011/10/09)
The first SeO2 induced (Z)-selective allylic alcohol formation of dialkyl alkylidenesuccinates has been demonstrated to accomplish one-step syntheses of several essential butenolides and fused butenolides via an unusual E- to Z- carbon-carbon d
An Efficient Entry Into Butenolides: Synthesis Of (+/-) Mintlactone
Chavan, Subhash P.,Zubaidha, P. K.,Ayyangar, Nagaraj R.
, p. 4605 - 4608 (2007/10/02)
Osmylation of β,γ-unsaturated esters and acid catalysed cyclisation of the resultant diols generate butenolides in high yields.
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