18 タキサン型ジテルペンの合成研究 その1

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概要

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• In the synthetic studies on biologically active taxane-type diterpenes, which possess a characteristic tricarbocyclic skeleton comprising 6-,8-, and 6-membered ring systems, we have first attempted the building-up of the optically active basic skeleton, taxa-4(16),11-diene(2) and its enantiomer(ent-2), according to the anti-synthetic route shown in Fig.1. I. Synthesis of 1,1,2-Trimethylcyclopentane Deriv. In order to prepare the starting compounds for synthesis of segment(A), four 1,1,2-trimethylcyclopentane deriv.(8,10,16,18) have been synthesized from d-camphor(3). II. Ring Enlargement of 1,1,2-Trimethylcyclopentane Deriv. Treatment of a vinyl deriv.(8) with 2,4,4,6-tetrabromocyclohexadienone(TBCO) afforded a desired ring-enlarged product(19), while the TBCO treatment of another vinyl deriv.(16) gave only two 5-membered ring compounds(21,22). In the case of an allyl alcohol (18), the BF_3-etherate treatment brought about the formation of two ring-enlarged products(25,26). Among three ring-enlarged products, 19 was considered to be the most favorable key compound for the synthesis of ent-2. III. Synthesis of ent-Taxa-4(16),11-diene(ent-2) A dithiane deriv.(29) was prepared by reaction of m-dithiane with an epoxide(28), which was derived from 19 via 27. 29 was then converted to a C_<12> compound(32, segment(A)) through 30 and 31. A iodomethyl deriv.(34), prepared from 32 via 33, was then coupled with 1,5-dimethoxy-1,4-cyclohexadiene to furnish a C_<18> compound (35). Derivation of 35 leading to ent-2 through 36 is under study and is discussed.

• 天然有機化合物討論会の論文
• 1979-09-20

著者

• 山本 佳男

  Faculty Of Pharmaceutical Sciences Osaka University

• 北川 勲

  阪大薬

• 藤岡 弘道

  Faculty Of Pharmaceutical Sciences Osaka University

• 梶原 彰治

  Faculty of Pharmaceutical Sciences, Osaka University

• 鈴木 賢治

  Faculty of Pharmaceutical Sciences, Osaka University

• 渋谷 博孝

  阪大薬

• 藤岡 弘道

  阪大薬

• 梶原 彰治

  阪大薬

• 山本 佳男

  阪大薬

• 高木 昭

  阪大薬

• 鈴木 賢治

  阪大薬

• 堀 学

  阪大薬

• 鈴木 賢治

  Faculty Of Pharmaceutical Sciences Osaka University

• 堀 学

  New Drug Research Laboratories, Kanebo Ltd.,

• 堀 学

  New Drug Research Laboratories Kanebo Ltd.

• 梶原 彰治

  Faculty Of Pharmaceutical Sciences Osaka University

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