Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2

doi:10.6023/cjoc202102021

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2820-2830.DOI: 10.6023/cjoc202102021 Previous Articles Next Articles

ARTICLES

基于分子内的仿生Diels-Alder反应构建Elansolid A1/A2的四氢茚烷核心结构

于奇^a, 杨帅^b, 唐聪云^a, 彭林^a^,^*(), 左之利^b^,^*(), 汪亮亮^b^,^*()

a 邵阳学院食品与化学工程学院湖南邵阳 422000
b 中国科学院昆明植物研究所昆明 650201

收稿日期:2021-02-06 修回日期:2021-03-30 发布日期:2021-04-06
通讯作者: 彭林, 左之利, 汪亮亮
基金资助:
中国科学院“西部之光”; 中国科学院青年创新促进会; 国家自然科学基金(21772207); 云南省千人计划; 湖南省教育厅(19c1655)

Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2

Qi Yu^a, Shuai Yang^b, Congyun Tang^a, Lin Peng^a(), Zhili Zuo^b(), Liangliang Wang^b()

a School of Food and Chemical Engineering, Shaoyang University, Shaoyang, Hunan 422000
b State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201

Received:2021-02-06 Revised:2021-03-30 Published:2021-04-06
Contact: Lin Peng, Zhili Zuo, Liangliang Wang
Supported by:
“Light of West China” Program; Youth Innovation Promotion Association of the Chinese Academy of Sciences; National Natural Science Foundation of China(21772207); “Thousand Talents Program” of Yunnan Province; Program from Education Department of Hunan Province(19c1655)

1. .pdf(2917KB)

Abstract

The Elansolid A1/A2 is metabolite from the gliding bacteriumChitinophaga sanctiiand shows antibiotic activity against Gram-positive bacteria. Up to now, the total synthesis of this natural product has not been reported yet due to its structure complexity, which arises from thetrans-tetrahydroindane unit and (Z)-(E)-(Z) triene motif as well as a 19-member macrolactone. In this study, two newO-functionalized substrates were synthesized to undergo the biomimetic intramolecular Diels-Alder reactions (IMDA) catalyzed by a chiral phosphoric acid to build the keytrans-tetrahydroindane core of Elansolid A1/A2 via a vinylicp-quinone methide intermediate. This result shows that an improveddr (1.8∶1) of IMDA reaction and shorter synthetic steps could be achieved.

Key words: biomimetic synthesis, Diels-Alder reaction, tetrahydroindane, elansolid

Cite this article

Qi Yu, Shuai Yang, Congyun Tang, Lin Peng, Zhili Zuo, Liangliang Wang. Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2820-2830.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

Figure 1. Elansolids natural products

Scheme 1. Reported biomimetic IMDA reaction and Lewis acid IMDA reaction respectively applied in the total synthesis of 20-deoxyl- Elansolid B1 and Elansolid B1

Figure 2. Devised O-functionalized IMDA substrates 1 and 2

Scheme 2. Synthesis of precursor 1 and biomimetic IMDA reaction DIPEA (diisopropylethylamine), DMP (dess-martin periodinane), NaHMDS (sodium bis(trimethylsilyl)amide), TBS, TMS (trimethylsilyl), TBAF, TBDPS (t-butyldiphenylsilyl), CPA (chiral phosphoric acid)

Scheme 3. Synthesis of precursor 2 and biomimetic IMDA reaction. LiHMDS (Lithium bis(trimethylsilyl)amide)

Scheme 4. Determination of the relative configuration of “Evans anti-aldol” product 6. DIBAL-H (diisobutylaluminum hydride), D-(+)-CSA (camphorsufonic acid)

References 11

[1]	Steinmetz, H.; Gerth, K.; Jansen, R.; Schlager, N.; Dehn, R.; Reinecke, S.; Kirschning, A.; Meller, R. Angew. Chem.,Int. Ed. 2011, 50,532. doi: 10.1002/anie.201005226
[2]	(a) Jansen, R.; Gerth, K.; Steinmetz, H.; Reinecke, S.; Kessler, W.; Kirschning, A.; Meller, R. Chem.-Eur. J. 2011, 17,7739. doi: 10.1002/chem.v17.28
	(b) Dehn, R.; Katsuyama, Y.; Weber, A.; Gerth, K.; Jansen, R.; Steinmetz, H.; Hofle, G.; Meller, R.; Kirschning, A. Angew. Chem.,Int. Ed. 2011, 50,3882. doi: 10.1002/anie.201006880
[3]	Wang,L. -L.; Kirschning, A. Beilstein J. Org. Chem. 2017, 13,1280. doi: 10.3762/bjoc.13.124
[4]	Weber, A.; Dehn, R.; Schlager, N.; Dieter, B.; Kirschning, A. Org. Lett. 2014, 16,568. doi: 10.1021/ol403441c
[5]	Wang,L. -L.; Candito, D.; Drager, G.; Herrmann, J.; Meller, R.; Kirschning, A. Chem.-Eur. J. 2017, 23,5291. doi: 10.1002/chem.201605884
[6]	Wang,L. -L.; Candito, D.; Dräger, G.; Kirschning, A. Eur. J. Org. Chem. 2017,5582.
[7]	Walker,M. A.; Heathcock,C. H. J. Org. Chem. 1991, 56,5747. doi: 10.1021/jo00020a006
[8]	Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74,87. doi: 10.1021/cr60287a005
[9]	Sun, H.; Abbott,J. R.; Roush,W. R. Org. Lett. 2011, 13,2734. doi: 10.1021/ol200834p
[10]	Our selected recent study on chiral phosphoric acid CPA:. Wang,L. -L.; Jiang, T.; Li,P. -H.; Sun,R. -J.; Zuo, Z. Adv. Synth. Catal. 2018, 360,4832. doi: 10.1002/adsc.201801329
[11]	Selected reviews and examples on chiral phosphoric acid: (a) Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114,9047. doi: 10.1021/cr5001496
	(b) Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2017, 117,10608. doi: 10.1021/acs.chemrev.7b00197
	(c) Li, S.; Lü, J.; Luo, S. Acta Chim. Sinica 2018, 76,869 (in Chinese). doi: 10.6023/A18060227
	( 李速家, 吕健, 罗三中, 化学学报, 2018, 76,869.)
	(d) Zhang, L.; Luo, S.; Cheng,J. -P. Angew. Chem.,Int. Ed. 2013, 52,9786. doi: 10.1002/anie.201304561

[1]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.
[2]	Wenjing Ma, Lizhi Zhu, Mengxun Zhang, Chising Lee. Asymmetric Synthesis of AB Rings in ent-Kaurene Carbon Framework [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 580-589.
[3]	Jun Zhao, Jian Xiao, Yawen Wang, Yu Peng. Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2933-2945.
[4]	Yuanzhi Li, Mengqian Zhu, Liang Xu. A Concise Biogenetically Inspired Formal Synthesis of Camptothecin [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2885-2890.
[5]	Gang Yang, Xiangyu Feng, Congcong Han, Yang Chen, Shuzhong He. Synthesis of the ABC Ring System of Wallichanol Natural Product [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 726-730.
[6]	Feng Qin, Lin Tang, Fei Huang, Xiaoyue Li, Wu Zhang. Copper-Catalyzed Three-Component Synthesis of Quinolines via Oxidation and Aza-Diels-Alder Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 318-324.
[7]	Zhang Yan, Guo Liandong, Xu Jing. Efficient Synthesis of the AC Ring System of Daphnilactone B [J]. Chin. J. Org. Chem., 2019, 39(4): 1079-1084.
[8]	Cai Zhengjun, Gao Jianbao, Li Bai, Zhong Yuan, Feng Xing, Xue Jijun, Jiang Xianxing. Application of [4+2]Cycloaddition Reaction of Tetrazine with Cyclooctyne in the Construction of Pyridazine Structure with Axial Chirality [J]. Chin. J. Org. Chem., 2018, 38(5): 1138-1146.
[9]	Liu Wenxiang, Wu Yuqiang, Li Lingzhi, Li Xia. Progress on the Asymmetric Diels-Alder Reaction of α,β-Unsaturated Carbonyl Compounds [J]. Chin. J. Org. Chem., 2016, 36(7): 1501-1512.
[10]	Yan Jinyi, Yang Zhusheng, Yang Nianfa. Synthesis and Optical Properties of Helical Poly[(S)-3-hydroxyl- diphenylmethyl-3'-vinyl-2,2'-dihydroxy-1,1'-binaphthyl] and Its Use in Asymmetric Hetero-Diels-Alder Reaction [J]. Chin. J. Org. Chem., 2016, 36(4): 812-817.
[11]	Meng Jin, Du Liyue, Guo Liucheng. Synthesis of Arylnaphthalene Lignan Lactones [J]. Chin. J. Org. Chem., 2016, 36(11): 2723-2728.
[12]	Chen Haixia, Liu Yan, Hu Bei, Zhao Mengmeng, Ren Kai, Xie Xiaomin, Xu Hao, Zhang Zhaoguo. Synthesis of Exo-norborn-5-ene-2,3-anhydride via Isomerization [J]. Chin. J. Org. Chem., 2015, 35(8): 1759-1764.
[13]	Zheng Ruoshan, Zhu Shifa. Application of o-Quinodimethanes in Organic Synthesis [J]. Chin. J. Org. Chem., 2014, 34(7): 1322-1339.
[14]	Zhou Nini, Shi Qian, Xie Zhixiang. Total Synthesis of Lycogarubin C and Lycogalic Acid A [J]. Chin. J. Org. Chem., 2014, 34(6): 1104-1109.
[15]	Yang Weifang, Xu Xiaoli, Zhang Zhanbin. Synthesis and Application of 1-(Pyridin-2-yl)-2-azabuta-1, 3-dienes [J]. Chin. J. Org. Chem., 2014, 34(6): 1161-1166.

基于分子内的仿生Diels-Alder反应构建Elansolid A1/A2的四氢茚烷核心结构

Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 11

Related Articles 15

Recommended Articles

Metrics

Comments