催化NH吲哚的C2异戊烯基化反应: 肽后期多样化和两步全合成tryprostatin B

doi:10.1016/S1872-2067(20)63780-9

催化学报 ›› 2021, Vol. 42 ›› Issue (9): 1593-1607.DOI: 10.1016/S1872-2067(20)63780-9

催化NH吲哚的C2异戊烯基化反应: 肽后期多样化和两步全合成tryprostatin B

呼延成^a^,^b^,^†, 李莹^a^,^b^,^†, 季定纬^a^,^b, 刘恒^a^,^b, 郑浩^a^,^b, 张功^a^,^b, 陈庆安^a^,^b^,^*()

^a中国科学院大连化学物理研究所, 辽宁大连116023
^b中国科学院大学, 北京100049

收稿日期:2021-01-02 接受日期:2021-02-07 出版日期:2021-09-18 发布日期:2021-05-16
通讯作者: 陈庆安
作者简介:^* 电话: (0411)84379260; 传真: (0411)84379223; 电子信箱: qachen@dicp.ac.cn
第一联系人：
^†共同第一作者
基金资助:
国家自然科学基金(21801239);国家自然科学基金(22071239)

Catalytic C2 prenylation of unprotected indoles: Late-stage diversification of peptides and two-step total synthesis of tryprostatin B

Yan-Cheng Hu^a^,^b^,^†, Ying Li^a^,^b^,^†, Ding-Wei Ji^a^,^b, Heng Liu^a^,^b, Hao Zheng^a^,^b, Gong Zhang^a^,^b, Qing-An Chen^a^,^b^,^*()

^aDalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^bUniversity of Chinese Academy of Sciences, Beijing 100049, China

Received:2021-01-02 Accepted:2021-02-07 Online:2021-09-18 Published:2021-05-16
Contact: Qing-An Chen
About author:^* Tel: +86-411-84379260; Fax: +86-411-84379223; E-mail: qachen@dicp.ac.cn
Qing-An Chen (Dalian Institute of Chemical Physics, Chinese Academy of Sciences) was born in 1984 in Fujian Province, China. He received a B.S. degree from University of Science and Technology of China in 2007 and earned his Ph.D. from Dalian Institute of Chemical Physics under the supervision of Prof. Yong-Gui Zhou in 2012. He worked with Prof. Vy M. Dong at the University of California Irvine as a postdoctoral fellow from 2012 to 2015. Then he joined Prof. Martin Oestreich's group at Technische Universitat Berlin as an Alexander von Humboldt Fellow. In 2017 he began his independent research career at the Dalian Institute of Chemical Physics, Chinese Academy of Sciences, where currently he is Professor of Chemistry. His research interests include the development of catalytic alkene functionalization, asymmetric synthesis and biomimetic catalysis. He has authored over 44 publications and 20 patents. In 2020, he received Thieme Chemistry Journal Award and was appointed as a young member of Editorial Board (2020-2024) of Chinese Journal of Catalysis.First author contact:
^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21801239);National Natural Science Foundation of China(22071239)

摘要/Abstract

摘要：

异戊烯基化吲哚生物碱是一类同时具有吲哚环和类异戊二烯基团的天然产物, 主要来源于各种真菌中. 异戊烯基的存在可以增强化合物的亲脂性, 使其能够更容易地穿过脂溶性的细胞膜与靶蛋白相结合, 因此, 这类天然产物往往表现出优异的生物活性. 例如, 从烟曲霉中分离的吲哚生物碱tryprostatins A和B是由L-色氨酸和L-脯氨酸组合而成, 在吲哚骨架C2位连有异戊烯基, 具有高效的抗肿瘤活性. 在已知的全合成中, 关键步骤C2位异戊烯基的引入, 均是通过多步当量反应实现的. 从原子和步骤经济性角度出发, 发展高效催化方法实现NH吲哚C2位直接异戊烯基化反应具有重要的意义. 但是由于吲哚的氮原子和C3位亲核性都较强, 使得挑战很大.
在生物体中, 吲哚生物碱C2位异戊烯基的引入是通过酶催化实现的. 二甲基烯丙基焦磷酸(DMAPP)先在酶作用下, 生成异戊烯基碳正离子, 然后与吲哚C2位进行傅克反应, 引入异戊烯基. 受这一生物过程启发, 设想通过化学方法能够生成稳定的异戊烯基碳正离子, 也可能实现吲哚C2异戊烯基化反应. 本文采用廉价易得的1,1-二甲基烯丙醇为异戊烯基前体, 对该想法进行了尝试. 首先, 以色醇为模板底物, 对酸催化剂、溶剂及反应温度进行了筛选. 在1,2-二氯乙烷(DCE)溶剂中, 布朗斯特酸、路易斯酸和固体酸都能促进反应的进行, 但会得到吲哚N和C2异戊烯基化两种产物, 其中三氯化铝有较好的收率和选择性. 通过对不同溶剂考察发现, 2-甲基四氢呋喃是最佳溶剂, 在80°C下反应, 目标产物收率为75%, 产物选择性可达到12:1. 随后, 对不同类型的3-取代吲哚进行了普适性考察. 对于色醇类底物, 吲哚苯环上的取代基以及N上的保护基对反应影响不大, 都能很顺利地参与反应. 在标准条件下, 色胺的异戊烯基化反应会发生在C3位, 而以氯苯为溶剂时, 可以提高C2位选择性, 通过该方法可在抗衰老分子褪黑素(melatonin)的C2位引入异戊烯基. 3-苯基和烷基取代的吲哚也是合适的底物.
肽的后期修饰在生物医药中有着很重要的用途, 因此, 本文也将该异戊烯基化反应尝试用于修饰色氨酸类衍生物. 保护的L-色氨酸酯以及色氨醇都能够顺利发生转化, 以中等收率得到目标产物. L-色氨酸与其它各类氨基酸如甘氨酸、丙氨酸、亮氨酸、异亮氨酸、苯丙氨酸、甲硫氨酸、天冬氨酸等形成的肽也可进行C2异戊烯基化反应. 此外, 该转化过程中, 可以完全保持手性, 不会发生消旋化. 特别是, L-色氨酸与L-脯氨酸酯形成的环二肽brevianamide F, 在该条件下, 也能发生C2位异戊烯基化反应, 快速合成天然吲哚生物碱tryprostatin B.
该反应有两种可能的路径, 一种是吲哚C2位直接异戊烯基化, 另一种是吲哚C3位先异戊烯基化, 然后再重排到C2位. 为进一步探索机理, 对其进行了研究. 首先, 在标准条件下, 3-酯基吲哚可以发生反应, C2位异戊烯基化产物收率为25%. 然后, 预先将异戊烯基引入C3位, 合成了3-酯基-3-异戊烯基-3H吲哚, 同样反应条件下, 也能检测到目标产物, 但收率只有5%. 其次, 以氘代1,1-二甲基烯丙醇为原料时, 3-异戊烯基吲哚也能与其发生反应, 并且在C3和C2位都观察到了氘代异戊烯基, 两种产物比例为1:2, 结果表明两种反应路径都是存在的, 但吲哚C2位直接异戊烯基化是主要路径.
此外, 以固体酸Nafion为催化剂, 离子液体[Bmim]Cl为反应介质, 在120°C时, 3-取代吲哚与1,1-二甲基烯丙醇的反应选择性会发生改变, 得到C2位异戊烯基异构化的产物.
总之, 以商业可得的1,1-二甲基烯丙醇为前体, 首次实现了化学催化NH吲哚C2位直接异戊烯基化反应, 获得较好的区域和化学选择性. 该方法能够兼容各类官能团, 底物适用性广, 且可以用于褪黑素以及色氨酸衍生各种肽类化合物的后期修饰. 基于该催化方法, 可以两步全合成天然吲哚生物碱tryprostatin B, 极大提高了合成效率, 有助于实现放大生产. 在固体酸/离子液体催化体系中, 还实现了反应选择性的改变, 丰富了产物类型.

关键词: 吲哚异戊烯基化, 步骤经济性, 原子经济性, 色氨酸, 肽多样化, 全合成

Abstract:

C2 prenylated indoles are widespread in a variety of bioactive natural alkaloids. Therefore, the selective installation of prenyl group at C2 position of NH indoles is of great significance. However, the known protocols generally require a multi-step procedure and stoichiometric promoters. Herein we develop a one-step C2 prenylation of NH indole with cheap tert-prenyl alcohol enabled by acid catalysis. Salient features include good regioselectivity, step- and atom-economy, broad substrate scope, and simple catalytic system. The mechanistic investigations demonstrate that both C2 prenylation and C3 prenylation/migration pathways are engaged in the reaction. Notably, this practical strategy can be applied to the late-stage diversification of tryptophan-based peptides and concise synthesis of tryprostatin B.

Key words: Indole prenylation, Step economy, Atom economy, Tryptophan, Peptide diversification, Total synthesis

呼延成, 李莹, 季定纬, 刘恒, 郑浩, 张功, 陈庆安. 催化NH吲哚的C2异戊烯基化反应: 肽后期多样化和两步全合成tryprostatin B[J]. 催化学报, 2021, 42(9): 1593-1607.

Yan-Cheng Hu, Ying Li, Ding-Wei Ji, Heng Liu, Hao Zheng, Gong Zhang, Qing-An Chen. Catalytic C2 prenylation of unprotected indoles: Late-stage diversification of peptides and two-step total synthesis of tryprostatin B[J]. Chinese Journal of Catalysis, 2021, 42(9): 1593-1607.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(20)63780-9

https://www.cjcatal.com/CN/Y2021/V42/I9/1593

图/表 8

Fig. 1. Representative C2 prenylated indole alkaloids.

Fig. 2. An overview on C2 prenylation of NH indoles.

Table 1 Optimization of C2 prenylation of tryptophol. a


Entry	Acid	Solvent	T (°C)	Yield ^b (%)	3a:3a’ ^c
1	CSA	DCE	70	39	3:1
2	Tf₂NH	DCE	70	22	4:1
3	AlCl₃	DCE	70	46	5:1
4	FeCl₃	DCE	70	29	10:1
5	Bi(OTf)₃	DCE	70	Mixture	—
6	Sc(OTf)₃	DCE	70	Mixture	—
7	BF₃·Et₂O	DCE	70	Mixture	—
8	Amberlyst-15 ^d	DCE	70	57	4:1
9	Nafion ^e	DCE	70	54	3:1
10	AlCl₃	PhCl	70	56	10:1
11	AlCl₃	NMP	70	N.R.	—
12	AlCl₃	dioxane	70	69	12:1
13	AlCl₃	THF	70	66	10:1
14	AlCl₃	2-MeTHF	70	67	12:1
15	AlCl₃	2-MeTHF	80	75	12:1
16	Al(OTf)₃	2-MeTHF	80	Mixture	—
17	AlMe₃	2-MeTHF	80	N.R.	—
18	Cu(OTf)₂	2-MeTHF	80	N.R.	—
19	Zn(OTf)₂	2-MeTHF	80	19	5:1
20	Mg(ClO₄)₂	2-MeTHF	80	N.R.	—
21	Al(OⁱPr)₃	2-MeTHF	80	N.R.	—
22	Al(OⁱPr)₃/HCl ^f	2-MeTHF	80	46	6:1

Fig. 3. Catalytic C2 prenylation of 3-substituted indoles. Reaction conditions: 1 (0.40 mmol), 2 (1.20 mmol), AlCl3 (10 mol%-30 mol%), 2-MeTHF or PhCl (0.40 mL), 80 °C, 24 h. Isolated yields were given. The ratio (3/3’) was determined by 1H NMR, unless otherwise stated, the ratio was > 20:1. a AlCl3 (30 mol%). b Amberlyst-15 (12.0 mg), 100 °C for 24 h. c Nafion (9.4 mg).

Fig. 4. Late-stage prenylation of tryptophanate and peptide. Reaction conditions: 4 (0.40 mmol), 2 (1.20 mmol), AlCl3 (30 mol%), PhCl (0.40 mL), 80 °C, 24 h. Isolated yields were given. The ratio (5/5’) was determined by 1H NMR, unless otherwise stated, the ratio was > 20:1.

Fig. 5. Concise synthesis of tryprostatin B and cyclodipeptide.

Fig. 6. Mechanistic investigation.

Fig. 7. Isomerization of prenyl group. Reaction conditions for one-step procedure: 1 (0.40 mmol), 2 (2.40 mmol), Nafion (9.4 mg), [Bmim]Cl (0.50 g), 120 °C, 24 h. [Bmim]Cl = 1-Butyl-3-methylimidazolium chloride.

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催化NH吲哚的C2异戊烯基化反应: 肽后期多样化和两步全合成tryprostatin B

Catalytic C2 prenylation of unprotected indoles: Late-stage diversification of peptides and two-step total synthesis of tryprostatin B

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