Studies toward Total Synthesis of Non-Aromatic Erythrinan Alkaloids. 7. Synthesis of Cocculolidine Skeleton
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概要
- 論文の詳細を見る
The skeletal structure of cocculolidine (1), a D-nor-erythinan alkaloid, was synthesized as the 8-oxo derivative 2 by several routes via the diester 4 as a key intermediate. One route was an ozonolysis of 14,15,17-trimethoxy-8-oxo-erythrinan (3) to directly yield 4 in 63%. The other was the Ce(IV) methanesulfonate oxidation of 16,17-dimethoxy-8-oxo-erythinan (6) to yield the p-quinone 7 (94%), which was converted to the same diester 4 by ozonolysis and peroxide oxidation (70%). The diester 4 was transformed to the corresponding anhydride 5,which was regioselectively reduced with a bulky borohydride (K-selectride^[○!R]) to give the desired lactone 2.
- 公益社団法人日本薬学会の論文
- 1998-12-15
著者
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毛利 邦彦
Showa College Of Pharmaceutical Sciences
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Tsuda Yuko
Faculty Of Pharmaceutical Science Kobe Gakuin University
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TSUDA YOSHISUKE
Faculty of Pharmaceutical Sciences, Kanazawa University
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ISOBE Kimiaki
Showa College of Pharmaceutical Sciences
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MOHRI Kunihiko
Showa Pharmaceutical University
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Mohri K
Showa College Of Pharmaceutical Sciences
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Isobe K
Showa College Of Pharmaceutical Sciences
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Isobe Kimiaki
Showa Pharmaceutical University
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MAEDA Manabu
Showa College of Pharmaceutical Sciences
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TAKEDA Taroh
Showa College of Pharmaceutical Sciences
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OHKUBO Ryoko
Showa College of Pharmaceutical Sciences
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Tsuda Yoshisuke
Faculty Of Pharmaceutical Sciences Kanazawa University
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Tsuda Y
Faculty Of Pharmaceutical Sciences And High Technology Research Center Kobe Gakuin University
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