Synthetic Studies on a Picrotoxane Sesquiterpene, Coriamyrtin. III. Completion of the Stereocontrolled Total Synthesis of (±)-Coriamyrtin
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概要
- 論文の詳細を見る
The stereocontrolled total synthesis of (±)-coriamyrtin (1) has now been completed, starting from protoanemonin and 2-methyl-1,3-cyclopentanedione, through fifteen steps. The Wittig reaction of the ditetrahydrofuranyl ether (3) with triphenylphosphonium methylide gave the exo-methylenic compound (4), which was derived to the lactone (6) by consecutive hydrolysis, alkaline hydrolysis, and lactonization. The lactone (6) was transformed into the bromoether (8), which was subjected to allylic hydroxylation to give the allyl alcohol (10). Epoxidation of the allyl alcohol (10) provided selectively the epoxy-alcohol (11), which was derived to the mesylate (16). Elimination of the O-mesyl group gave the olefin (17). Epoxidation of 17 with m-chloroperbenzoic acid gave (±)-bromocoriamyrtin (18) and finally, reductive debromination of 18 furnished (±)-coriamyrtin (1).
- 公益社団法人日本薬学会の論文
- 1983-06-25
著者
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内山 文昭
Faculty Of Pharmaceutical Sciences Kyoto University
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犬伏 康夫
Faculty of Pharmaceutical Sciences, Kyoto University
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田中 圭
Faculty Of Pharmaceutical Sciences Kyoto University
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田中 圭
静岡県大 薬
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犬伏 康夫
Faculty Of Pharmaceutical Sciences Kyoto University
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坂元 清志
Faculty of Pharmaceutical Sciences, Kyoto University
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田中 圭
京都大学薬学部
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坂元 清志
Faculty Of Pharmaceutical Sciences Kyoto University
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田中 圭
Faculty of Eng., Oita Univ.
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