Lycophlegmarineの合成研究(第1報)ピリジン-無水トリフルオロ酢酸-酸素によるエポキシ化およびFawcettimineの形式合成
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In connection with synthetic study of lycophlegmarine, stereoselective synthesis of the allyl alcohol (D : R=CF_3), which was an intermediate of fawcettimine synthesis, was investigated. In that occasion, acylation of 1 and 2 in pyridine with (CF_3CO)_2O overnight gave mainly the unexpected epoxide (5) and (6), respectively. Acylation with pyridine-(CF_3CO)_2O under oxygen atmosphere gave only the epoxide for 3 h, and acylation with NEt_3-(CF_3CO)_2O or pyridine-Ac_2O afforded the corresponding diacyl olefin even under oxygen atmosphere. Moreover, epoxides (5) and (6) were converted to the allyl alcohol (D : R=CF_3) in a high yield via the same ketone (B=10). This means that stereoselective and formal synthesis of fawcettimine was achieved.
- 社団法人日本薬学会の論文
- 1983-11-25
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