1 α-アミノ酸から光学活性Carene骨格の合成研究 : (+)-Car-2-eneの合成

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概要

• 論文の詳細を見る

• For a total synthesis of the optically active carene derivatives from optically active α-amino acids, several attempts were made on intramolecular cyclization of 2-cyclohexenyl esters of α-substituted-α-diazo acetic acid (3) which were derived from diazotization of the corresponding amino acid esters. Results of model reactions are shown in Table II. One of the optically active diastereoisomers (12) which was obtained by resolution of 2-cyclohexenyl-L-alaninate was diazotized by treatment with isoamylnitrite and then cyclized using Cu powder as a catalyst to afford the optically active lactone (15). (15) was then converted into the key intermediate (17) having the bicyclo[4.1.0] heptane ring system, from which (+)-car-2-ene was synthesized via the sequence, (17)→(18)→(19)→(20)→(21)→(22)→(23)→(+)-car-2-ene.

• 天然有機化合物討論会の論文
• 1974-10-01

著者

• 高村 則夫

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 溝口 富茂

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• Koga Kenjiro

  Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hokuriku University

• 高村 則夫

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 古賀 憲司

  東大薬

• 山田 俊一

  東大薬

• 高村 則夫

  東大薬

• 溝口 富茂

  田辺製薬有機研

• 溝口 富茂

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

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