5957-56-2Relevant academic research and scientific papers
DIASTEREOSELECTIVE SYNTHESIS OF β- AND γ2-MUUROLENE: A CARBOCATIONIC PATHWAY FROM MONO- TO SESQUITERPENES
Azizur-Rahman,Klein, Herbert,Dressel, Juergen,Mayr, Herbert
, p. 6041 - 6046 (2007/10/02)
The Lewis acid catalysed addition of the piperityl chlorides 6 to isoprene yields adduct 7, which undergoes a cis-stereoselective cyclisation to give the diastereoisomeric muurolene monohydrochlorides 8.Treatment with potassium tert-butoxide affords β- an
CHEMISTRY OF THE ORGANOSILICON COMPOUNDS-165 2-TRIMETHYLSILYL-METHYL-1, 3-BUTADIENE-A VERSATILE BUILDING BLOCK FOR TERPENE SYNTHESIS
Sakurai, Hideki,Hosomi, Akira,Saito, Masaki,Sasaki, Koshi,Iguchi, Hirokazu,et al.
, p. 883 - 894 (2007/10/02)
Two types of synthetically useful reactions of 2-trimethylsilylmethyl-1,3-butadiene (7) are discussed.Reactions of 7 with acid chlorides, aldehydes, ketones and acetals activated by a Lewis acid give isoprenylated compounds, while 7 undergoes the Diels-Alder reaction whit dienophiles.High regiospecificity of the reaction qualifies 7 for a versatile building block of terpene synthesis.
A New Synthesis of (+/-)-γ2-Cadinene
Vig, O. P.,Sharma, M. L.,Taneja, K. C.,Verma, N. K.
, p. 972 - 973 (2007/10/02)
8-Isopropyl-5-methylene-2-oxo-decalin (II) on nucleophilic epoxidation with dimethyloxosulphonium methylide under nitrogen atmosphere gives the epoxide (III) which undergoes stereoselective cleavage with lithium diisopropylamide to furnish the allylic alcohol, 2-hydroxymethyl-8-isopropyl-5-methyl-Δ2-decalene (IV).Conversion of IV into the corresponding mesylate (V) using mesyl chloride/TEA in dry dichloromethane and subsequent reduction of V with LAH yields (+/-)-γ2-cadinene (I).
