Total Syntheses of (±)-Crinine, (±)-Crinamine, and (±)-6a-epi-Crinamine via the Regioselective Synthesis and Diels−Alder Reaction of 3-Aryl-5-bromo-2-pyrone

Total Syntheses of (±)-Crinine, (±)-Crinamine, and (±)-6a-epi-Crinamine via the Regioselective Synthesis and Diels−Alder Reaction of 3-Aryl-5-bromo-2-pyrone

We have devised a new unified synthetic protocol to (±)-crinine, (±)-crinamine, and (±)-6a-epi-crinamine from the Diels−Alder cycloadduct of 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone with TBS vinyl ether. The requisite 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone was prepared from the C3-select...

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Veröffentlicht in:Journal of organic chemistry 2008-08, Vol.73 (16), p.6258-6264
Hauptverfasser: Tam, Nguyen Thanh, Chang, Jayhyok, Jung, Eun-Ju, Cho, Cheon-Gyu
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Sprache:eng
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Amaryllidaceae Alkaloids - chemical synthesis
Pyrones - chemistry
Stereoisomerism
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container_end_page 6264
container_issue 16
container_start_page 6258
container_title Journal of organic chemistry
container_volume 73
creator Tam, Nguyen Thanh
Chang, Jayhyok
Jung, Eun-Ju
Cho, Cheon-Gyu
description We have devised a new unified synthetic protocol to (±)-crinine, (±)-crinamine, and (±)-6a-epi-crinamine from the Diels−Alder cycloadduct of 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone with TBS vinyl ether. The requisite 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone was prepared from the C3-selective Stille coupling reaction of 3,5-dibromo-2-pyrone. Also noted is that the vinyl bromide can be used as a handle for further derivatization.
doi_str_mv 10.1021/jo8008353
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subjects Amaryllidaceae Alkaloids - chemical synthesis
Pyrones - chemistry
Stereoisomerism
title Total Syntheses of (±)-Crinine, (±)-Crinamine, and (±)-6a-epi-Crinamine via the Regioselective Synthesis and Diels−Alder Reaction of 3-Aryl-5-bromo-2-pyrone
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