1. 毕业设计（论文）的内容和要求

内容 吲哚啉类生物碱是一类重要的天然产物，由于其数目众多、结构复杂，同时往往具有显著的生理活性，因此一直备受合成化学家以及药物化学家的青睐。

多环吲哚啉是一系列具有重要生理活性的生物碱如马钱属（strychnos）家族生物碱、白坚木属（aspidosperma）家族生物碱和长春花（vinca）家族生物碱的基本骨架。

论文选题以色胺为起始原料研究高效构建多环吲哚啉化合物骨架的基本方法，合成的产物具有重要的实际应用价值。

2. 参考文献

[1] Martin D B, Vanderwal C D. Efficient access to the core of the Strychnos, Aspidosperma and Iboga alkaloids. A short synthesis of norfluorocurarine[J]. J. Am. Chem. Soc., 2009,131(10):3472~3473. [2] Hong A Y, Vanderwal C D. A synthesis of alsmaphorazine B demonstrates the chemical feasibility of a new biogenetic hypothesis[J]. J. Am. Chem. Soc., 2015,137(23):7306~7309. [3] Zhu J, Liang Y, Wang L, et al. Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines[J]. J. Am. Chem. Soc., 2014,136(19):6900~6903. [4] Zhu J, Cheng Y, Kuang X, et al. Highly Efficient Formal [2 2 2] Strategy for the Rapid Construction of Polycyclic Spiroindolines: A Concise Synthesis of 11-Demethoxy-16-epi-myrtoidine[J]. Angew. Chem. Int. Ed., 2016,55(32):9224~9228. [5] Roy S, Eastman A, Gribble G W. Synthesis of N-alkyl substituted bioactive indolocarbazoles related to G#246;6976[J]. Tetrahedron, 2006,62(33):7838~7845. [6] Tantak M P, Gupta V, Nikhil K, et al. Sequential one-pot synthesis of bis(indolyl)glyoxylamides: Evaluation of antibacterial and anticancer activities[J]. Bioorg Med Chem Lett, 2016,26(13):3167~3171. [7] Vanderwal C D. Reactivity and synthesis inspired by the Zincke ring-opening of pyridines[J]. J Org Chem, 2011,76(23):9555~9567. [8] Paton R S, Steinhardt S E, Vanderwal C D, et al. Unraveling the mechanism of cascade reactions of zincke aldehydes[J]. J Am Chem Soc, 2011,133(11):3895~3905. [9] Martin D B, Nguyen L Q, Vanderwal C D. Syntheses of strychnine, norfluorocurarine, dehydrodesacetylretuline, and valparicine enabled by intramolecular cycloadditions of Zincke aldehydes[J]. J Org Chem, 2012,77(1):17~46. [10] Benayad S, Ahamada K, Lewin G, et al. Preakuammicine: A Long-Awaited Missing Link in the Biosynthesis of Monoterpene Indole Alkaloids[J]. Eur J Org Chem, 2016,2016(8):1494~1499. [11] Michels T D, Rhee J U, Vanderwal C D. Synthesis of δ-Tributylstannyl-α,β,γ,δ-Unsaturated Aldehydes from Pyridines[J]. Org Lett, 2008,10(21):4787~4790. [12] Jones S B, Simmons B, MacMillan D W C. Nine-Step Enantioselective Total Synthesis of ( )-Minfiensine[J]. J Am Chem Soc, 2009,131(38):13606~13607. [13] Horning B D, MacMillan D W C. Nine-Step Enantioselective Total Synthesis of (#8722;)-Vincorine[J]. J Am Chem Soc, 2013,135(17):6442~6445. [14] Laforteza B N, Pickworth M, MacMillan D W C. Enantioselective Total Synthesis of (#8722;)-Minovincine in Nine Chemical Steps: An Approach to Ketone Activation in Cascade Catalysis[J]. Angew Chem Int Ed, 2013,52(43):11269~11272 [15] Mejia-Oneto J M, Padwa A. Intramolecular [3 2]-cycloaddition reaction of push-pull dipoles across heteroaromatic pi-systems[J]. Org Lett, 2004,6(19):3241~3244. [16] 谢卫青, 左智伟, 资伟伟, 等. 分子内氧化偶联反应在合成复杂吲哚生物碱骨架中的应用[J]. 有机化学, 2013(05).

3. 毕业设计（论文）进程安排

2016.12-2017.02 查阅文献，了解底物性质，设计实验思路 2017.02-2017.05 底物合成，并进行合成路线尝试 2017.05-2017.06 数据整理，书写毕业论文准备答辩