330173-08-5Relevant articles and documents
Synthesis of (±)-rolipram
Chang, Meng-Yang,Sun, Pei-Pei,Chen, Shui-Tein,Chang, Nein-Chen
, p. 1865 - 1872 (2007/10/03)
A facile synthesis of rolipram via stepwise [3+2] annulation and desulfonated hydrolysis was reported. Base-induced coupling/cyclization reactions of α-sulfonylacetamide with (Z)-2-bromoacrylic ester yielded three contiguous centers on the pyroglutamate system with trans-trans orientation as the one-pot key step.
Synthesis of fused bicyclic glutarimides
Chang, Meng-Yang,Chen, Chung-Yi,Chen, Shui-Tein,Chang, Nein-Chen
, p. 7547 - 7553 (2007/10/03)
We describe an efficient route towards the synthesis of fused bicyclic glutarimides using facile [3+3] reaction of α-sulfonylacetamides with different α,β-unsaturated esters as the key step. Intramolecular cyclization of 4-substituted 3-sulfonylglutarimide to form 5,6-, 6,6- or 6,7-fused bicyclic glutarimides was accomplished via alkylation, oxidative cyclization or ring-closing metathesis in modest yield.
Regioselective reduction of 3-sulfonyl glutarimides to 3,4-dihydro-5-sulfonylpyridin-2-ones. Formal synthesis of the indolizidine 8a-epi-dendroprimine
Hsu, Ru-Ting,Cheng, Li-Ming,Chang, Nein-Chen,Tai, Huo-Mu
, p. 5044 - 5047 (2007/10/03)
Sodium borohydride regioselectively reduced various 3-sulfonyl glutarimides 1 to hydroxy piperidones 2, which were further dehydrated to 3,4-dihydro-5-sulfonylpyridin-2-ones 3 in the presence of boron trifluoride. Formal synthesis of 8a-epi-dendroprimine (4) possessing an indolizidine ring system has been accomplished via intramolecular radical cyclization of cyclic vinyl sulfone 5.