Highly Stereoselective Total Synthesis of Pikronolide, the Aglycon of the First Macrolide Antibiotic Pikroraycin. Crucial Role of Benzyl-Type Protecting Groups Removable by 2,4-Dichloro-5,6-dicyanobenzoquinone Oxidation(Organic,Chemical)

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• The first total synthesis of pikronolide, the aglycon of pikromycin, isolated as the first macrolide antibiotic, is described. Two segments i (5: C-1-C-10) and ii (6: C-11-C-15) were synthesized highly stereoselectively from D-glucose and coupled by Yamaguchi's method to give the ester (17), which was subjected to macrocyclization by means of the intramolecular Wittig-Horner reaction developed by Nicolaou, and the 14-membered cyclic enone (18) was isolated in excellent yield. Removal of protecting groups and Swern oxidation gave pikronolide (2). In this synthesis, 3,4-dimcthoxybenzyl, 4-methoxybenzyl, and benzyl protecting group for hydroxy function played a crucial role.

• 公益社団法人日本薬学会の論文
• 1987-06-25

著者

• 中島 範行

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• 及川 裕二

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 米光 宰

  岡山理大理

• 米光 宰

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 及川 裕二

  北大薬

• 中島 範行

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• 米光 宰

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 浜田 辰夫

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 田中 達義

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 浜田 辰夫

  北大薬

• 田中 達義

  Faculty Of Pharmaceutical Sciences Hokkaido University

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