title: Regioselective reduction of 3-sulfonyl glutarimides to 3,4-dihydro-5-sulfonylpyridin-2-ones. Formal synthesis of the indolizidine 8a-epi-dendroprimine.
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.
authors.affiliation: Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, Taiwan 804, Republic of China.
authors.forename: Ru-Ting
authors.initials: RT
authors.lastname: Hsu
authors.forename: Li-Ming
authors.initials: LM
authors.lastname: Cheng
authors.forename: Nein-Chen
authors.initials: NC
authors.lastname: Chang
authors.forename: Huo-Mu
authors.initials: HM
authors.lastname: Tai