108653-79-8Relevant academic research and scientific papers
Enantioselective Synthesis of the Functionalized Bicycloheptane Derivatives, Key Intermediates for the Chiral Synrhesis of Santalenes and Santalols
Arai, Yoshitsugu,Yamamoto, Masatoshi,Koizumi, Toru
, p. 1225 - 1228 (1986)
Optically active functionalized bicycloheptane derivatives obtained by the asymmetric Diels-Alder cycloaddition of ethyl p-tolylsulfinylmethylenepropionate with cyclopentadiene provide the potentially useful intermediates for synthesis of bicyclic sesquiterpenes such as (+)-epi-β-stanalene.
The Asymmetric Diels-Alder Cycloaddition Using Ethyl(-)-(Z)-(R)s-2-methyl-3-(p-tlylsulfinyl)propenoate: Application to an Enantioselective Synthesis of (+)-epi-β-Santalene
Arai, Yoshitsugu,Yamamoto, Masatoshi,Koizumi, Toru
, p. 467 - 474 (2007/10/02)
The Diels-Alder reaction of ethyl (-)-(Z)-(R)s-2-methyl-3-(p-tolylsulfinyl)propenoate (6) with cyclopentadiene gave the adducts, 7, 8, and 9 in a high diastereoselective manner.The cycloadduct 7 was transformed into the acetal (-)-25.The racemic 25 was used as an intermediate in the synthesis of (+/-)-β-santalol.Thus, the chiral acetal (-)-25 should provide a route to (-)-Β-santalol.The cycloadduct 8 was converted into (+)-epi-β-santalene in 11 steps.
