Synthetic Studies on Lythraceae Alkaloids. V. Total Synthesis of (±)-Vertaline

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概要

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• The first total synthesis of one of the cis-quinolizidine Lythraceae alkaloids, vertaline (IV), was described. The Mannich reaction of isopelletierine (V) with 6-bromoveratraldehyde (VI) in tetrahydrofuran in the presence of aqueous sodium hydroxide gave the cis-and trans-quinolizidine (VII and VIII) in the ratio of 5 : 2. Reduction of VII with sodium borohydride afforded the axial alcohol (IX) along with the equatorial alcohol (X). The Ullmann condensation of the acetyl derivative (XI) from IX with methyl 3-(4-hydroxyphenyl) propionate furnished the biphenyl ether (XIII). Hydrolysis of XIII and lactonization of the resulting hydroxy-acid (XV) provided (±)-vertaline (IV).

• 社団法人日本薬学会の論文
• 1976-05-25

著者

• 小川 信男

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 荒田 義雄

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 花岡 美代次

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 花岡 美代次

  金沢大学薬学部

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

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