Synthesis of (+)- and (-)-cis-α-Irones

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概要

• 論文の詳細を見る

• A stereocontrolled total synthesis of natural (+)-cis-α-irone (1) is described. The key intermediate (±)-hemiacetal 15 was prepared from the diene 10 in six steps. The crucial optical resolution of (±)-15 was achieved by initial stereoselective conversion into the corresponding l-menthyl acetals 16 and 17 followed by separation and hydrolysis. One of the optically pure enantiomers of 15 was transformed to (-)-18 and then to (+)-1 in seven steps. The synthetic (+)-1 was found to be identical with the natural (+)-cia-α-irone. The isomeric (-)-cis-α-irone was also synthesized from the other enantiomer of 15,via (+)-18.

• 公益社団法人日本薬学会の論文
• 1991-10-25

著者

• 大石 武

  Riken Institute (The Institute of Physical and Chemical Research)

• 大石 武

  Faculty Of Engineering Yokohama National University:(present Address)meiji College Of Pharmacy

• 大石 武

  理研:(現)明治薬科大学

• 伊藤 文隆

  Riken (the Institute Of Physical And Chemical Research)

• 大塚 晏央

  Faculty Of Engineering Yokohama National University:(present Address)pharmaceutical Research Center

• 大塚 晏央

  RIKEN (The Institute of Physical and Chemical Research)

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