Regioselective reduction of 3-sulfonyl glutarimides to 3,4-dihydro-5-sulfonylpyridin-2-ones. Formal synthesis of the indolizidine 8a-epi-dendroprimine

DOI: 10.1021/jo025539p

Source and publish data:

Journal of Organic Chemistry p. 5044 - 5047 (2002)

Update date:2022-09-26

Topics:

Authors:

Hsu, Ru-Ting

Cheng, Li-Ming

Chang, Nein-Chen

Tai, Huo-Mu

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Article abstract of DOI:10.1021/jo025539p

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.

Full text of DOI:10.1021/jo025539p

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