Regioselective reduction of 3-sulfonyl glutarimides to 3,4-dihydro-5-sulfonylpyridin-2-ones. Formal synthesis of the indolizidine 8a-epi-dendroprimine |
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| Authors: | Hsu Ru-Ting Cheng Li-Ming Chang Nein-Chen Tai Huo-Mu |
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| Institution: | Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, Taiwan 804, Republic of China. |
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| Abstract: | 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. |
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