A Regioselective Lithiation of ortho-Cresols Using the Bis(dimethylamino)phosphoryl Group as a Directing Group : General Synthesis of 2,3-Dihydrobenzo[b]furans Including Naturally Occurring Neolignans

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概要

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• A general synthetic method was developed for 2-aryl-2,3-dihydrobenzo[b]furans via regioselective lithiation of ortho-tolyl tetramethylphosphorodiamidates followed by addition of aromatic aldehydes as a key step. ortho-Tolyl tetramethylphosphorodiamidates were regioselectively lithiated with sec-BuLi in tetrahydrofuran at -105℃ to give benzylic lithio species. The resulting lithio species were reacted with aromatic aldehydes to provide 1,2-diarylethanolderivatives. Reductive removal of the phosphoryl group with lithium aluminum hydride followed by acidic treatment led to 2-aryl-2,3-dihydrobenzo[b]furans in good overall yields. The utility of this strategy was demonstrated in regioselective syntheses of highly substituted neolignan natural products, such as (±)-licarin B and (±)-carnatol, starting from O-bis(dimethylamino)phosphorylated eugenol or isoeugenol.

• 公益社団法人日本薬学会の論文
• 1991-12-25

著者

• 古川 淳

  School Of Pharmaceutical Sciences Nagasaki University

• 渡辺 三明

  Center For Instrumental Analysis Nagasaki University

• 川西 建司

  School of pharmaceutical Sciences Nagasaki University

• 秋吉 隆治

  School of pharmaceutical Sciences Nagasaki University

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