917611-85-9Relevant academic research and scientific papers
Catalytic diastereoselective polycyclization of homo(polyprenyl)arene analogues bearing terminal siloxyvinyl groups
Uyanik, Muhammet,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 5649 - 5652 (2007/10/03)
Highly diastereoselective polycyclization of homo(polyprenyl)arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4α(equatorial)- and 4β(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the 4α-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the 4β-preference.
Transannular Diels-Alder reaction studies with an activated dienophile. An enantioselective synthesis of an A.B.C.[6.6.6.] trans-syn-cis tricycle
Barriault, Louis,Quellet, Stephane G.,Deslongchamps, Pierre
, p. 14937 - 14956 (2007/10/03)
The synthesis and transannular Diels-Alder reaction of a chiral 14 membered trans-cis-cis (TCC) macrocyclic triene with an activated dienophile leading to an A.B.C.[6.6.6.] tricyclic compound are described. The outcome of the TADA reaction under thermal and catalyzed conditions is discussed.
