Cyclopentenone Annulation of 1,4-Diketones with Potassium Phosphate Tribasic : A Synthesis of a Monoterpene Alkaloid, (±)-Tecomanine

• 宮下 正昭

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 田中 大輔

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 白谷 智宣

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 入江 寛

  Faculty of Pharmaceutical Sciences, Nagasaki University

抄録

Conjugate addition of cyclohexanone lithium enolate to 2-nitro-2-butene and the Nef reaction on the resulting nitronate gave 2-(2-oxopropyl)cyclohexanone in good yield. Treatment of the 2-(2-oxopropyl)cyclohexanone thus obtained with potassium phosphate tribasic (K_3PO_4) in isopropanol gave 2,3,4,5,6,7-hexahydro-3-methyl-3aH-inden-2-one (8). Application of the procedure to 1,3-dimethyl-4-piperidone (11) gave the 1,3,4,6,7,7a-hexahydro-6-oxo-2,4,7-trimethyl-2H-2-pyrindine (12). Epimerization of 12 with basic alumina gave (±)-tecomanine (1). The short synthesis of the alkaloid demonstrates the usefulness of K_3PO_4 as a base for cyclopentenone annulation of 1,4-diketones without migration of the double bond.

収録刊行物

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 40 (6), 1614-1615, 1992-06-25

  公益社団法人日本薬学会

キーワード

• nitroolefin
• conjugate addition
• Nef reaction
• intramolecular aldol reaction
• cyclopentenone
• potassium phosphate tribasic
• monoterpene alkaloid
• tecomanine

詳細情報

• CRID: 1572824502208281088
• NII論文ID: 110003630047
• NII書誌ID: AA00602100
• ISSN: 00092363
• 本文言語コード: en
• データソース種別:
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