Synthetic Studies on Pseudoguaianolides. II. A Total Synthesis of (±)-Carpesiolin
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概要
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A total synthesis of (±)-carpesiolin (3) is reported starting from the hydroazulenone (2), which is a key intermediate of helenanolide synthesis. For the introduction of the C_6 to C_8 functionalities, 2 was converted to the epoxy-alcohol (5). Its structure was confirmed by chemical and spectroscopic evidence. After construction of the γ-lactone ring, the tert-butyl protective group was removed from the ester (15) by acid-catalyzed thermolysis. However, this reaction was unexpectedly accompanied by concomitant 1,3-acyl migration with inversion of the configuration at C_4 to yield the hydroxy-ester (16), whose structure was established by analysis of its proton magnetic resonance spectrum and some chemical reactions. After manipulation of the protective group to give the tetrahydropyranyl ether (18), its conversion to (±)-carpesiolin was achieved by (i) introduction of the exo-methylene group onto the lactone ring, (ii) oxidation to the cyclopentanone (24), and (iii) deprotection of the C_6 hydroxyl group.
- 公益社団法人日本薬学会の論文
- 1983-02-25
著者
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金 相元
Faculty of Pharmaceutical Sciences, Josai University
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金 相元
Faculty Of Pharmaceutical Sciences Josai University
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Kim S‐w
Faculty Of Pharmaceutical Sciences Josai University
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長尾 惠四郎
Faculty Of Pharmaceutical Sciences Josai University
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千葉 昌人
Faculty Of Pharmaceutical Sciences Josai University
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