大家｜Mo Movassaghi ——复杂天然产物全合成、有机新反应

Key Word

Total Synthesis

Complex Nature Product

 New reactions

Introduction

Mohammad Movassaghi目前是麻省理工学院（MIT）化学系教授。

他在1991年考入加州大学伯克利分校（UB Berkeley），在Paul Allan Bartlett教授（斯坦福大学Willam Summer Johnson教授子弟）指导下，获得化学理学学士学位。1995年，Mo加入哈佛大学（Harvard）Andrew G. Myers教授（哈佛大学E. J. Corey子弟）团队，在加州理工学院和哈佛大学进行联合培养，2001年获得哈佛大学有机化学博士学位。同年，他加入哈佛大学Eric N. Jacobsen教授课题组，从事有机化学领域的博士后研究。

2003年，加入麻省理工学院，担任研究助理教授，2008年升任副教授，2013年提拔为正教授，至今仍在MIT从事化学领域研究。

Mo带领团队，主要专注于结构复杂天然产物的全合成研究，并在这些研究过程中，开发新的反应类型。

Mo团队至今为止，团队网站上公开发表文章不足百位数。但是，其中不乏Science、JACS、ACIE、Chem. Soc.等文章。由此可见，Mo Movassaghi研究工作做得非常出色。

Education & Research

Awards & Honors

Teaching

Research Interst

Movassaghi团队的研究兴趣是广义的合成有机化学，包括复杂的天然产物合成，以及发现和开发新的有机合成反应。该研究团队的重点是合成有趣的结构和生物学相关的自然产物，为方法学的进一步发展和详细的机理研究提供一个平台。这些合成努力，旨在发展包括催化和不对称过程的新颖有机合成方法。

复杂分子的合成，启迪高选择性反应的发展，为合成新策略的开发提供了平台。Movassaghi团队特别感兴趣于结构复杂和化学复杂的天然产物，它们的合成需要最高水平的选择性和效率。靶点的选择是基于新的分子结构，重要的生物活性，和潜在的机制研究来解决化学的基本问题，此外还提供关于其生物作用模式的见解。基于预测的自然产物的生物遗传途径的策略，不仅可以改善我们对其生物合成的认知，而且还有助于模拟自然创造分子复杂性的效率。

Movassaghi团队研究的核心兴趣是：设计、发现和发展具有广泛应用于有机化学的高选择性反应。这些研究活动的重要组成部分包括：旨在更好地理解涉及反应性和选择性的基本原理的机制研究。

Selected Publications

“Structure and Function of NzeB, a Versatile C–C and C–N Bond Forming Diketopiperazine Dimerase.” Shende, V. V.; Khatray, Y.; Newmister, S. A.; Sanders, J.; Lindovska, P.; Yu, F.; Doyon, T.; Houk. K. N.; Movassaghi, M.; Sherman, D. H. J. Am. Chem. Soc. 2020,142, 17413–17424.

“n→π* Interactions modulate the disulfide reduction potential of epidithiodiketopiperazines.” Kilgore, H. R.; Olsson, C. R.; D'Angelo, K. A.; Movassaghi, M.; Raines, R. T. J. Am. Chem. Soc. 2020,142, 15107–15115.

“Synthesis of Potent Cytotoxic Epidithiodiketopiperazines Designed for Derivatization.” Olsson, C. R.; Payette, J. N.; Cheah, J. H.; Movassaghi, M. J. Org. Chem. 2020, 85, 4648-4662.

“Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives.” Pompeo, M. M.; Cheah, J. H.; Movassaghi, M. J. Am. Chem. Soc. 2019, 141, 14411-14420.

“Mechanism of Permanganate Promoted Dihydroxylation of Complex Diketopiperazines: Critical Roles of Counter-Cation and Ion-Pairing.” Haines, B. E.; Nelson, B. M.; Grandner, J. M; Kim, J.; Houk, K. N; Movassaghi, M.; Musaev, D. G. J. Am. Chem. Soc. 2018, 140 (41), 13375–13386.

“Concise Synthesis of (–)-Hodgkinsine, (–)-Calycosidine, (–)-Hodgkinsine B, (–)-Quadrigemine C, and (–)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines.” Lindovska, P.; Movassaghi, M. J. Am. Chem. Soc. 2017 139 (48), 17590-17596.

“Quantitative Modeling of Bis(pyridine)silver (I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates.” Bischoff, A. J.; Nelson, B. M.; Niemeyer, Z. L.; Sigman, M. S.; Movassaghi, M. J. Am. Chem. Soc. 2017, 139 (43), 15539-15547.

“Enantioselective Total Synthesis of (–)-Deoxoapodine.” Kang, T.; White, K. L.; Mann, T. J.; Hoveyda, A. H.; Movassaghi, M. Angew. Chem. Int. Ed. 2017, 56, 13857

“Synthesis and Evaluation of Agelastatin Derivatives as Potent Modulators for Cancer Invasion and Metastasis.” Antropow, A. H.; Xu, K.; Buchsbaum, R. J.; Movassaghi, M. J. Org. Chem. 2017, 82, 7720-7731.

“Concise Total Syntheses of (+)-Haplocidine and (+)-Haplocine Via Late-Stage Oxidation of (+)-Fendleridine Derivatives.” White, K. L.; Movassaghi, M. J. Am. Chem. Soc. 2016, 138, 11383-11389.

“Convergent and Biomimetic Enantioselective Total Synthesis of (−)-Communesin F.” Lathrop, S. P.; Pompeo, M.; Chang, W.-T. T.; Movassaghi, M. J. Am. Chem. Soc. 2016, 138, 7763-7769.

“Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.” Loach, R. P.; Fenton, O. S.; Movassaghi, M. J. Am. Chem. Soc. 2016, 138, 1057-1064.

“The fibroblast Tiam1-osteopontin pathway modulates breast cancer invasion and metastasis.” Xu, K.; Tian, X.; Oh, S. Y.; Movassaghi, M.; Naber, S. P.; Kuperwasser, C.; Buchsbaum, R. J. Breast Cancer Res. 2016, 18, 14.

“Direct Observations of Intermediates Involved in the Bischler-Napieralski Reaction.” White, K. L.; Mewald, M.; Movassaghi, M. J. Org. Chem. 2015, 80, 7403-7411.

“Biogenetically-Inspired Total Synthesis of Epidithiodiketopiperazines and Related Alkaloids.” Kim, J.; Movassaghi, M. Acc. Chem. Res. 2015, 48, 1159-1171.

“Concise and Enantioselective Total Synthesis of (−)-Mehranine, (−)-Methylenebismehranine, and Related Aspidosperma Alkaloids.” Mewald, M.; Medley, J. W.; Movassaghi, M. Angew. Chem. Int. Ed. 2014, 53, 11634-11639.

“Application of Diazene-Directed Fragment Assembly to the Total Synthesis and Stereochemical Assignment of (+)-Desmethyl-meso-chimonanthine and Related Heterodimeric Alkaloids ” Lathrop, S. P.; Movassaghi, M. Chem. Sci. 2014, 5, 333-340.

Recent Publications

“‍‍‍‍‍‍‍‍‍Structure and Function of NzeB, a Versatile C–C and C–N Bond Forming Diketopiperazine Dimerase.” Shende, V. V.; Khatray, Y.; Newmister, S. A.; Sanders, J.; Lindovska, P.; Yu, F.; Doyon, T.; Houk. K. N.; Movassaghi, M.; Sherman, D. H. J. Am. Chem. Soc. 2020,142, 17413–17424.

“n→π* Interactions modulate the disulfide reduction potential of epidithiodiketopiperazines.” Kilgore, H. R.; Olsson, C. R.; D'Angelo, K. A.; Movassaghi, M.; Raines, R. T. J. Am. Chem. Soc. 2020,142, 15107–15115.

“Synthesis of Potent Cytotoxic Epidithiodiketopiperazines Designed for Derivatization.” Olsson, C. R.; Payette, J. N.; Cheah, J. H.; Movassaghi, M. J. Org. Chem. 2020, 85, 4648-4662.

“Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives.” Pompeo, M. M.; Cheah, J. H.; Movassaghi, M. J. Am. Chem. Soc. 2019, 141, 14411-14420.

“Mechanism of Permanganate Promoted Dihydroxylation of Complex Diketopiperazines: Critical Roles of Counter-Cation and Ion-Pairing.” Haines, B. E.; Nelson, B. M.; Grandner, J. M; Kim, J.; Houk, K. N; Movassaghi, M.; Musaev, D. G. J. Am. Chem. Soc. 2018, 140 (41), 13375–13386.

“Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.” Antropow, A. H.; Garcia, N. R.; White, K.; Movassaghi, M. Org. Lett. 2018 , 20 , 3647-3650.

“Concise Total Synthesis of (+)-Asperazine A and (+)-Pestalazine B.” Nelson, B. M.; Loach, R. P.; Schiesser, S.; Movassaghi, M. Org. Biomol. Chem. 2018, 16, 202-207.

“Synthesis of Antibiotics and Related Molecules. ” Movassaghi, M. van der Donk, W. A. J. Org. Chem. 2018 , 83 , 6826–6828.

“Biogenetic Considerations. ” Movassaghi, M. Tetrahedron 2018 , 74 , 5583.

“Concise Synthesis of (–)-Hodgkinsine, (–)-Calycosidine, (–)-Hodgkinsine B, (–)-Quadrigemine C, and (–)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines.” Lindovska, P.; Movassaghi, M. J. Am. Chem. Soc. 2017, 139, 17590-17596.

“Quantitative Modeling of Bis(pyridine)silver (I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates.” Bischoff, A. J.; Nelson, B. M.; Niemeyer, Z. L.; Sigman, M. S.; Movassaghi, M. J. Am. Chem. Soc. 2017, 139, 15539-15547.

“Enantioselective Total Synthesis of (–)-Deoxoapodine.” Kang, T.; White, K. L.; Mann, T. J.; Hoveyda, A. H.; Movassaghi, M. Angew. Chem. Int. Ed. 2017, 56, 13857.

“Synthesis and Evaluation of Agelastatin Derivatives as Potent Modulators for Cancer Invasion and Metastasis.” Antropow, A. H.; Xu, K.; Buchsbaum, R. J.; Movassaghi, M. J. Org. Chem. 2017, 82, 7720-7731.

“Concise Total Syntheses of (+)-Haplocidine and (+)-Haplocine Via Late-Stage Oxidation of (+)-Fendleridine Derivatives.” White, K. L.; Movassaghi, M. J. Am. Chem. Soc. 2016, 138, 11383-11389.

“Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.” Lathrop, S. P.; Pompeo, M.; Chang, W.-T. T.; Movassaghi, M. J. Am. Chem. Soc. 2016, 138, 7763-7769.

“Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.” Loach, R. P.; Fenton, O. S.; Movassaghi, M. J. Am. Chem. Soc. 2016, 138, 1057-1064.

“The fibroblast Tiam1-osteopontin pathway modulates breast cancer invasion and metastasis.” Xu, K.; Tian, X.; Oh, S. Y.; Movassaghi, M.; Naber, S. P.; Kuperwasser, C.; Buchsbaum, R. J. Breast Cancer Res. 2016, 18, 14.

The Group

Mo独立研究至今，也为化学领域培养了不少人才，一下列举数位：

在MIT任职的人员有：Sydney Creutz, Diana Hunt, Alison Ondrus, Grazia Piizzi

Sunkyun Han在KAIST，Matthew M. Pompeo在Genentech公司，Stephen Lathrop在Colorado State，Taek Kang在韩国科技研究院，Giovanni Piersanti在乌尔比诺大学……

简评

Mo教授带领团队，每年发表四五篇研究成果，相对而言，这个产出数量一般。认真研读他们发表的文章，会发现他们对所从事、研究领域对热爱与深入。正是专注与深入，才可以产出高水平的研究成果。

The Group Website

http://web.mit.edu/movassag/www/index.htm

阅读更多

• 大家 ｜ 世界著名化学家
• 药企 ｜ 科研到实用转化
• 反应 ｜ 人名反应：知识储备
• 合成 ｜ 有机化学的皇冠
• 实用 ｜ 实用技巧+数据表格