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(－)-Isochaetominine推测结构的对映选择性全合成与结构修正

黄培强 ,  茅中一 ,  耿辉

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引用本文: 黄培强, 茅中一, 耿辉. (－)-Isochaetominine推测结构的对映选择性全合成与结构修正[J]. 有机化学, 2016, 36(2): 315-324. doi: 10.6023/cjoc201512015 shu
Citation:  Huang Peiqiang, Mao Zhongyi, Geng Hui. Enantioselective Total Synthesis and Structural Revision of (－)-Isochaetominine[J]. Chinese Journal of Organic Chemistry, 2016, 36(2): 315-324. doi: 10.6023/cjoc201512015 shu

(－)-Isochaetominine推测结构的对映选择性全合成与结构修正

  • 1.

    福建省化学生物学重点实验室 能源材料化学协同创新中心 厦门大学化学化工学院化学系 厦门 361005

    • 通讯作者: 黄培强
  • 基金项目:

    国家自然科学基金(No. 21472153) (No. 21472153)

    教育部长江学者和创新团队发展计划资助项目 

摘要: 报道生物碱isochaetominine推测结构8的对映选择性全合成与结构修正. 采用立体多样性合成策略, 通过L-色氨酸与L-丙氨酸苄酯组合, 以DMDO氧化启动的串联反应为关键反应, 经5步高效地完成了isochaetominine推测结构8及其立体异构体(+)-2,3,14-tri-epi-chaetominine (12)的全合成. 基于本实验室此前有关毛壳菌素(1)立体多样性合成的工作, 天然isochaetominine的结构修正为(－)-11-epi-chaetominine (18). 我们此前已完成了该天然产物的首次对映选择性全合成(从L-色氨酸出发, 5步, 总产率31.6%). 此外, 通过研究色氨酸与缬氨酸叔丁酯组合, 建立了isochaetominine C三个非对映立体异构体的立体多样性合成. 最后, 证实了化合物13B无法进行C(14)位定点差向异构化, 但可以进行C(11)和C(14)双差向异构化.

English

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    43. [43] After arriving at the conclusions of this paper, we informed the corresponding author of the reference 36 about the correct structure of the natural isochaetominine. In line with the information we provided, the authors prepared a single crystal of the natural isochaetominine and determined its structure by X-ray diffraction analysis. Their new result confirmed our conclusions. For the corrections to the Ref. [36], see: Xie, F.; Li, X.-B.; Zhou, J.-C.; Xu, Q.-Q.; Wang, X.-N.; Yuan, H.-Q.; Lou, H.-X.; Chem. Biodiversity 2015, 12, 1954.[43] After arriving at the conclusions of this paper, we informed the corresponding author of the reference 36 about the correct structure of the natural isochaetominine. In line with the information we provided, the authors prepared a single crystal of the natural isochaetominine and determined its structure by X-ray diffraction analysis. Their new result confirmed our conclusions. For the corrections to the Ref. [36], see: Xie, F.; Li, X.-B.; Zhou, J.-C.; Xu, Q.-Q.; Wang, X.-N.; Yuan, H.-Q.; Lou, H.-X.; Chem. Biodiversity 2015, 12, 1954.

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  • 发布日期:  2015-12-15
  • 收稿日期:  2015-12-10
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