Efficient Chiral Induction by Diene Iron-Tricabonyl Moiety. IV. : Asymmetric Total Synthesis of a Piperidine Alkaloid, SS20846A

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概要

• 論文の詳細を見る

• By LiClO_4-catalyzed cycloaddition with Danishefsky's diene 5,an optically active 1-azatriene Fe(CO)_3 complex was converted into the 2-substituted dehydropiperidinone 8,from which a piperidine alkaloid 1 (SS20846A) was synthesized in an enantiomerically pure form via successive reduction and removal of the protecting groups. Although the reduction of the ketone 3 proceeded with cis-selectivity even with a hindered reducing agent, the desired trans-alcohol 4 could be obtained by the reaction with sodium borohydride in the presence of cerium(III) chloride. The cis-selective reduction of 3 originates from the equatorial attack of a hydride on conformer A, in which the diene Fe(CO)_3 moeity is axially oriented due to the severe steric hindrance with the p-methoxyphenyl (PMP) group on the nitrogen atom. However, the cerium salt reverses the stereoselectivity of the hydride reduction of 3.

• 社団法人日本薬学会の論文
• 1997-12-15

著者

• 竹本 佳司

  Faculty Of Pharmaceutical Sciences Osaka University

• 岩田 宙造

  阪大院薬

• Takemoto Yoshiji

  Faculty Of Pharmaceutical Sciences Osaka University

• Takemoto Y

  Graduate School Of Pharmaceutical Sciences Kyoto University

• UEDA Shigeo

  Faculty of Pharmaceutical Sciences, Osaka University

• TAKEUCHI Jun

  Faculty of Pharmaceutical Sciences, Osaka University

• BABA Yasutaka

  Faculty of Pharmaceutical Sciences, Osaka University

• IWATA Chuzo

  Faculty of Pharmaceutical Sciences, Osaka University

• Iwata Chuzo

  Faculty Of Pharmaceutical Sciences Osaka University

• Ueda S

  Faculty Of Pharmaceutical Sciences Osaka University

• Ueda Shigeo

  Faculty Of Pharmaceutical Sciences Osaka University

• Takeuchi J

  Department Of Materials Science Shimane University

• Takeuchi J

  Department Of Physics Faculty Of Science Shimane University

• Baba Yasutaka

  Faculty Of Pharmaceutical Sciences Osaka University

• Takeuchi J

  Faculty Of Pharmaceutical Sciences Osaka University

• Takeuchi Jun

  Faculty Of Pharmaceutical Sciences Hokkaido University:department Of Laboratory Medicine Nagoya Univ

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