Problem Set

Lab Hall D319, 7:00 pm, every Saturday.
Open to public, please contact Xudong Yang at xyang@nankai.edu.cn.

DATE

03/13/2021
03/20/2021

LECTURE

Total Synthesis of XXXXXX.
Total Synthesis of XXXXXX.

NAME

Juwei Ma
Le Chang


(+)-Peniciketal A

03/06/2021 Bingjian Wang
Total Synthesis of (+)-Peniciketals A and B.
Yifan Deng, Chia-Ping H. Yang, and Amos B. Smith.*
J. Am. Chem. Soc. 2021, 143, 17401744.
[Problem and Key]

(+)-Stephadiamine

02/27/2021 Xudong Yang
Total Synthesis of (+)-Stephadiamine.
Minami Odagi*, Taisei Matoba, and Kazuo Nagasawa.*
J. Am. Chem. Soc. 2021, 143, 26992704.
[Problem and Key]

Tetrodotoxin

01/30/2021 Junhong Yang
Total Synthesis of Tetrodotoxin.
Keigo Murakami, Tatsuya Toma, and Satoshi Yokoshima.*
Angew. Chem. Int. Ed. 2020, 59, 62536257.
[Problem and Key]

(−)-Lepenine

01/25/2021 Le Chang
Total Synthesis of (−)-Lepenine.
Yoshitake Nishiyama, Yuki Han-ya, and Tohru Fukuyama.*
J. Am. Chem. Soc. 2014, 136, 65986601.
[Problem and Key]

(−)-Ambiguine P

01/16/2021 Juwei Ma
Total Synthesis of (−)-Ambiguine P.
Jiasu Xu, and Viresh H. Rawal.*
J. Am. Chem. Soc. 2019, 141, 48204823.
[Problem and Key]

(−)-Mitrephorone A

01/09/2021 Bingjian Wang
Total Synthesis of (−)-Mitrephorone A.
Michael Schneider, Matthieu J. R. Richter, and Erick M. Carreira.*
J. Am. Chem. Soc. 2020, 142, 1780217809.
[Problem and Key]

(+)-Caldaphnidine J

01/04/2021 Haiming Zhang
Asymmetric total synthesis of (+)-caldaphnidine J.
Lian-Dong Guo, Yan Zhang, and Jing Xu.*
Nat. Commun. 2020, 11, 3538.
[Problem and Key]

Dankasterone A

12/19/2020 Qunlong Zhang
Total Synthesis of Dankasterones A and B and Periconiastone A.
Pengquan Chen, Cheng Wang, and Zhiqiang Ma.*
Angew. Chem. Int. Ed. 2021, 60, 2–9.
[Problem and Key]

4β-Acetoxyprobotryane-9β,15α-diol

12/12/2020 Yang Kuang
Total Synthesis of 4β-Acetoxyprobotryane-9β,15α-diol.
Wen Zhang, Zi-Xiong Zhou, and Chuang-chuang Li.*
J. Am. Chem. Soc. 2020, 142, 19868–19873.
[Problem and Key]

(+)-Haperforin G

12/05/2020 Jia Ke
Total Synthesis of (+)-Haperforin G.
Wei Zhang, Zhenyu Zhang, and Zhen Yang.*
J. Am. Chem. Soc. 2020, 142, 19487–19492.
[Problem and Key]

Arcutinidine

11/28/2020 Le Chang
Total Synthesis of Arcutinidine.
Shupeng Zhou, Kaifu Xia, and Ang Li.*
J. Am. Chem. Soc. 2019, 141, 13718–13723.
[Problem and Key]

Kopsinitarine E

11/21/2020 Juwei Ma
Total Synthesis of Kopsinitarine E.
Karre Nagaraju, Dongshun Ni, and Dawei Ma.*
Angew. Chem. Int. Ed. 2020, 59, 1–5.
[Problem and Key]

(+)-Rubriflordilactone A

11/14/2020 Bingjian Wang
Total Synthesis of (+)‐Rubriflordilactone A.
Shermin S. Goh, Guihem Chaubet, and Edward A. Anderson.*
Angew. Chem. Int. Ed. 2015, 54, 12618–12621.
[Problem and Key]

(–)-Curvulamine

11/07/2020 Xudong Yang
Total Synthesis of (−)-Curvulamine.
Karl T. Haelsig, Jun Xuan, and Thomas J. Maimone.*
J. Am. Chem. Soc. 2020, 142, 1206–1210.
[Problem and Key]

(–)-Daphnezomine A

10/31/2020 Quanlong Zhang
Total Synthesis of (−)-Daphnezomines A and B.
Guangpeng Xu, Jinbao Wu, and Chao Li.*
J. Am. Chem. Soc. 2020, 142, 15240–15245.
[Problem and Key]

Liangshanone

10/24/2020 Haiming Zhang
Total Synthesis of Liangshanone.
Hong-Xiu Huang, Fen Mi, and Yong Qin.*
Angew. Chem. Int. Ed. 2020, 59, 1–7.
[Problem and Key]

Viridin

10/17/2020 Jia Ke
Total Synthesis of Viridin and Viridiol.
Yang Ji, Zhengyuan Xin, and Shuanhu Gao.*
J. Am. Chem. Soc. 2019, 141, 16208–16212.
[Problem and Key]

Picrotoxinin

10/10/2020 Kuang Yang
Total Synthesis of picrotoxinin.
Homer L. Pearce, and E. J. Corey.*
J. Am. Chem. Soc. 1979, 79, 5841–5843.
[Problem and Key]

(–)-Cajanusine

09/26/2020 Jia Ke
Total Synthesis of (−)-Cajanusine.
Renyu Guo, Brittany P. Witherspoon, and M. Kevin Brown.*
J. Am. Chem. Soc. 2020, 142, 5002–5006.
[Problem and Key]

Macfarlandin C

09/19/2020 Xudong Yang
Total Synthesis of Macfarlandin C.
Tyler K. Allred, Andre P. Dieskau, and Larry E. Overman.*
Angew. Chem. Int. Ed. 2020, 132, 6327–6331.
[Problem and Key]

(+)-Cornexistin

09/12/2020 Xudong Yang
Total Synthesis of (+)‐Cornexistin.
Christian Steinborn, Raphael E. Wildermuth, and Thomas Magauer*
Angew. Chem. Int. Ed. 2020, 59, 17282–17285.
[Problem and Key]

()-Bactobolin A

09/05/2020 Xudong Yang
Total Synthesis of (−)-Bactobolin A.
Petra Vojackova, Lucyna Michalska, and Jakub Svenda*
J. Am. Chem. Soc. 2020, 142, 7306–7311.
[Problem and Key]

()-Conidiogenone

08/29/2020 Yang Kuang
Total Synthesis of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol.
Bo Xu, Wen Xun, and Hongbin Zhai*
Angew. Chem. Int. Ed. 2020, 59, 16475–16479.
[Problem and Key]

()-Batrachotoxinin A

08/22/2020 Haiming Zhang
Total Synthesis of (−)-Batrachotoxinin A.
Yinliang Gao, Zhixian Guo, and Tuoping Luo*
J. Am. Chem. Soc. 2020, 142, 3675–3679.
[Problem and Key]

()-Rhodomollanol A

08/15/2020 Quanlong Zhang
Total Synthesis of (−)-Rhodomollanol A.
Jianhong Gao, Peirong Rao, and Hanfeng Ding*
J. Am. Chem. Soc. 2020, 142, 4592–4597.
[Problem and Key]

()-Picrotoxinin

08/08/2020 Xudong Yang
Total Synthesis of (−)-Picrotoxinin.
Steven W. M. Crossley, Guanghu Tong, and Ryan A. Shenvi*
J. Am. Chem. Soc. 2020, 142, 11376–11381.
[Problem and Key]

()-Scabrolide A

07/11/2020 Yang Kuang
Total Synthesis of (−)-Scabrolide A.
Nicholas J. Hafeman, Steven A. Loskot, and Brian M. Stoltz*
J. Am. Chem. Soc. 2020, 142, 8585–8590.
[Problem and Key]

()-Rostratiin A

07/04/2020 Yang Kuang
 Total Synthesis of (−)-Epicoccin G and (−)-Rostratin A.
Pierre Thesmar, and Olivier Baudoin*
J. Am. Chem. Soc. 2019, 141, 15779–15783.
[Problem and Key]

()Spirochensilide A

06/27/2020 Yang Kuang
Asymmetric Total Synthesis of (−)-Spirochensilide A.
Xin-Ting Liang, Jia-Hua Chen, and Zhen Yang*
J. Am. Chem. Soc. 2020, 142, 8116–8121.
[Problem and Key]

Amphilectene

06/20/2020 Yang Kuang
Total Synthesis of Amphilectene.
Sergey V. Pronin, and Ryan A. Shenvi*
J. Am. Chem. Soc. 2012, 134, 19604–19606.
[Problem and Key]

Pladienolide B

06/13/2020 Qunlong Zhang
Total Synthesis of the Potent Antitumor Macrolides Pladienolide B and D .
Regina M. Kanada, Daisuke Itoh, and Yoshihiko Kotake*
Angew. Chem. Int. Ed. 2007, 46, 4350–4355.
[Problem and Key]

(+)Waihoensene

06/06/2020 Yang Kuang
Asymmetric Total Synthesis of (+)-Waihoensene.
Yongzheng Qu, Zheyuan Wang, and Zhen Yang*
J. Am. Chem. Soc. 2020, 142, 6511–6515.
[Problem and Key]

Wickerol B

05/30/2020 Chuanke Chong
Divergent Synthesis of Antiviral Diterpenes Wickerols A and B.
Jiachen Deng, Yuhan Ning, and Jinghan Gui*
J. Am. Chem. Soc. 2020, 142, 4690–4695.
[Problem and Key]

(–)-Caldaphnidine O

01/16/2020 Yang Kuang
Enantioselective Total Synthesis of (−)-Caldaphnidine O.
Lian-Dong Guo, Jingping Hu, and Jing Xu*
J. Am. Chem. Soc. 2019, 141, 13043–13048.
[Problem and Key]

(–)-Illisimonin A

01/04/2020 Haiming Zhang
Total Synthesis and Structure Revision of (−)-Illisimonin A.
Alexander S. Burns and Scott D. Rychnovsky*
J. Am. Chem. Soc. 2019, 141, 13295–13300.
[Problem and Key]

(–)-Vinigrol

12/21/2019 Chuanke Chong
Total Synthesis of (–)-Vinigrol.
Long Min, Xiaohong Lin, and Chuang-Chuang Li*
J. Am. Chem. Soc. 2019, 141, 15773–15778.
[Problem and Key]

Epoxyeujindole A

12/07/2019 Jia Ke
Total Synthesis of Epoxyeujindole A.
Zhaohong Lu, Hailong Li, Ming Bian, and Ang Li*
J. Am. Chem. Soc. 2015, 137, 13764‒13767.
[Problem and Key]

Pharicin A

11/24/2019 Xudong Yang
Total Synthesis of Pharicin A.
Chi He, Jialei Hu, Yubing Wu, and Hanfeng Ding*
J. Am. Chem. Soc. 2017, 139, 6098–6101.
[Problem and Key]

(−)-Daphlongamine H

11/09/2019 Qunlong Zhang
Total Synthesis of (−)-Daphlongamine H.
Cedric L. Hugelshofer, Vignesh Palani, and Richmond Sarpong*
J. Am. Chem. Soc. 2019, 141, 8431−8435.
[Problem and Key]

Weisaconitine D

10/26/2019 Yang Kuang
Network-analysis-guided Synthesis of Weisaconitine D and Liljestrandinine.
C. J. Marth, G. M. Gallego, J. C. Lee, T. P. Lebold, S. Kulyk, K. G. M. Kou, J. Qin, R. Lilien, and R. Sarpong*
Nature 2015, 528, 493–498.
[Problem and Key]

Taiwaniadducts B

10/12/2019 Haiming Zhang
Total Synthesis of Taiwaniadducts B, C, and D.
Jun Deng, Shupeng Zhou, Wenhao Zhang, Jian Li, Ruofan Li, and Ang Li*
J. Am. Chem. Soc. 2014, 136, 8185−8188.
[Problem and Key]

Gracilamine

09/28/2019 Chuanke Chong
Total Synthesis of Gracilamine.
Yingbo Shi, Baochao Yang, Shujun Cai, and Shuanhu Gao*
Angew. Chem. Int. Ed. 2014, 53, 9539–9543.
[Problem and Key]

(±)-Communesin F

09/14/2019 Jia Ke
Total Synthesis of (±)-Communesin F.
Jun Yang, Haoxing Wu, Liqun Shen, and Yong Qin*
J. Am. Chem. Soc. 2007, 129, 13794–13795.
[Problem and Key]

(+)-Tubingensin A

08/30/2019 Xudong Yang
Total Synthesis of (+)-Tubingensin A.
Adam E. Goetz, Amanda L. Silberstein , Michael A. Corsello, and Neil K. Garg*
J. Am. Chem. Soc. 2014, 136, 3036–3039.
[Problem and Key]

(+)-Pleuromutilin

08/17/2019 Qunlong Zhang
Total Synthesis of (+)-Pleuromutilin.
Elliot P. Farney, Sean S. Feng, Felix Schäfers, and Sarah E. Reisman*
J. Am. Chem. Soc. 2018, 1404, 1267–1270.
[Problem and Key]

(−)-Indoxamycin A

08/03/2019 Chuanke Chong
Total Synthesis of (−)-Indoxamycins A and B.
Naifeng Hu, Changming Dong, Cuifang Zhang, and Guangxin Liang*
Angew. Chem. Int. Ed. 2019, 58, 6659–6662.
[Problem and Key]

Schindilactone A

07/20/2019 Jia Ke
Total Synthesis of (±)-Schindilactone A.
Qing Xiao, Wei-Wu Ren, Zhi-Xing Chen, Tian-Wen Sun, Yong Li, Qin-Da Ye, Jian-Xian Gong, Fan-Ke Meng, Lin You, Yi-Fan Liu, Ming-Zhe Zhao, Ling-Min Xu, Zhen-Hua Shan, Ying Shi, Ye-Feng Tang,* Jia-Hua Chen,* and Zhen Yang*
Angew. Chem. Int. Ed. 2011, 123, 7511–7515.
[Problem and Key]

(–)-N-Methylwelwitindolinone C Isothiocyanate

07/06/2019 Xudong Yang
Total Synthesis of (–)-N-Methylwelwitindolinone C Isothiocyanate.
Alexander D. Huters, Kyle W. Quasdorf, Evan D. Styduhar, and Neil K. Garg*
J. Am. Chem. Soc. 2011, 133, 15797–15799.
[Problem and Key]

(+)-Ryanodol

06/24/2019 Qunlong Zhang
Total Synthesis of (+)-Ryanodol.
Kangway V. Chuang, Chen Xu, and Sarah E. Reisman*
Science 2016, 353, 912–915.
[Problem and Key]

Minfiensine

06/10/2019 Chuanke Chong
Total Synthesis of Minfiensine.
Liqun Shen, Min Zhang, Yi Wu, and Yong Qin*
Angew. Chem. Int. Ed. 2008, 47, 3618−3621.
[Problem and Key]

Et-743

05/25/2019 Jia Ke
Total Synthesis of Et-743.
Weiming He, Zhigao Zhang, and Dawei Ma*
Angew. Chem. Int. Ed. 2019, 58, 3972–3975.
[Problem and Key]

(+)-Harringtonolide

05/11/2019 Xudong Yang
Total Synthesis of (+)-Harringtonolide.
Hai-Jun Zhang, Lin Hu, Zhiqiang Ma, Ruininng Li, Zhen Zhang, Cheng Tao, Bin Cheng, Yun Li, Huifei Wang, and Hongbin Zhai*
Angew. Chem. Int. Ed. 2016, 55, 11638–11641.
[Problem and Key]

(−)-Incarviatone A

04/27/2019 Qunlong Zhang
Total Synthesis of (−)-Incarviatone A.
Benke Hong, Chao Li, Zhen Wang, Jie Chen, Houhua Li*, and Xiaoguang Lei*
J. Am. Chem. Soc. 2015, 137, 11946–11949.
[Problem and Key]

Maoecrystal V

04/11/2019 Chuanke Chong
Total Synthesis of Maoecrystal V.
Jianxian Gong, Guang Lin, Wenbo Sun, Chuang-Chuang Li*,Zhen Yang*
J. Am. Chem. Soc. 2010, 132, 16745−16746.
[Problem and Key]

Rubriflordilactone A

03/30/2019 Jia Ke
Total Synthesis of Rubriflordilactone A
Jian Li, Peng Yang, Ming Yao, Jun Deng, and Ang Li*
J. Am. Chem. Soc. 2014, 136, 16477–16480.
[Problem and Key]

Ingenol

03/16/2019 Xudong Yang
Total Synthesis of Ingenol.
Lars Jorgensen, Steven J. McKerrall, Christian A. Kuttruff, Felix Ungeheuer,Jakob Felding, and Phil S. Baran*
Science 2013, 341, 878–882.
[Problem and Key]

Atropurpuran

03/02/2019 Qunlong Zhang
Total Synthesis of Atropurpuran.
Shengling Xie, Gui Chen, Hao Yan, Jieping Hou, Yongping He, Tongyun Zhao, and Jing Xu*
J. Am. Chem. Soc. 2019, 141, 3435–3439.
[Problem and Key]