Natural product total synthesis using rearrangement reactions

被引:23
作者
Chen, Lu [1 ,3 ]
Li, Guang [2 ]
Zu, Liansuo [3 ]
机构
[1] Fujian Agr & Forestry Univ, Coll Plant Protect, Key Lab Biopesticide & Chem Biol, Minist Educ, Fuzhou 350002, Fujian, Peoples R China
[2] Peking Union Med Coll & Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
[3] Tsinghua Univ, Sch Pharmaceut Sci, Beijing 100084, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 19期
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE TOTAL SYNTHESES; SKELETAL REARRANGEMENTS; AKUAMMILINE ALKALOIDS; COLLECTIVE SYNTHESES; A-C; DISCOVERY;
D O I
10.1039/d2qo01040b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of natural products has been an important pursuit in chemical synthesis due to their fascinating structural complexity and/or interesting biological activities. In most synthetic designs, the rapid construction of the core skeletons, the precise control of stereochemistry, and the identification of suitable synthons are key concerns, which, to a large extent, account for the overall synthetic efficiency. This review will highlight how rearrangement reactions can contribute in addressing these three concerns, thus simplifying the total synthesis campaigns.
引用
收藏
页码:5383 / 5394
页数:12
相关论文
共 50 条
[41]   Design, synthesis and spectroscopic characterisation of a focused library based on the polyandrocarpamine natural product scaffold [J].
Baron, Paul S. ;
Neve, Juliette E. ;
Camp, David ;
Suraweera, Lekha ;
Lam, Ann ;
Lai, John ;
Jovanovic, Lidija ;
Nelson, Colleen ;
Davis, Rohan A. .
MAGNETIC RESONANCE IN CHEMISTRY, 2013, 51 (06) :358-363
[42]   Design and Synthesis of Natural Product-Like Terphenyl as Potent Topoisomerase IIα Inhibitors [J].
Guan, Mengjia ;
Qiu, Jin ;
Lu, Chunhua ;
Zhao, Baobing ;
Shen, Yuemao .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (11) :3039-3047
[43]   Natural Product Gels and Their Gelators [J].
Zhi, Kangkang ;
Yang, Xin .
PROGRESS IN CHEMISTRY, 2019, 31 (09) :1314-1328
[44]   Natural product as a source of prodrug [J].
Padmavathy, Jagannathan ;
Saravanan, Devarajan .
BANGLADESH JOURNAL OF PHARMACOLOGY, 2017, 12 (02) :151-161
[45]   Chemography of Natural Product Space [J].
Miyao, Tomoyuki ;
Reker, Daniel ;
Schneider, Petra ;
Funatsu, Kimito ;
Schneider, Gisbert .
PLANTA MEDICA, 2015, 81 (06) :429-435
[46]   Synergistic approach for treatment of chicken coccidiosis using berberine - A plant natural product [J].
Malik, Tauseef Ahmad ;
Kamili, Azra N. ;
Chishti, M. Z. ;
Tanveer, Syed ;
Ahad, Shazia ;
Johri, R. K. .
MICROBIAL PATHOGENESIS, 2016, 93 :56-62
[47]   1,3-Diazepanes of Natural Product-Like Complexity from Cyanamide-Induced Rearrangement of Epoxy-δ-lactams [J].
Dutta, Sanjay ;
Higginson, Cody J. ;
Ho, Bao T. ;
Rynearson, Kevin D. ;
Dibrov, Sergey M. ;
Hermann, Thomas .
ORGANIC LETTERS, 2010, 12 (02) :360-363
[48]   A Common Precursor Approach to Structurally Diverse Natural Products: The Synthesis of the Core Structure of (±)-Clausenamide and the Total Synthesis of (±)-Hyalodendrin [J].
Szulc, Blanka R. ;
Sil, Bruno C. ;
Ruiz, Arnaud ;
Hilton, Stephen T. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (34) :7438-7442
[49]   Total synthesis of natural products containing bicyclo[n.2.2] ring systems [J].
Hou, Bao-Long ;
Liu, Junyang ;
Qiao, Chuang ;
Li, Chuang-Chuang .
TETRAHEDRON LETTERS, 2024, 135
[50]   Total synthesis of natural fregenedadiol and its diacetate, rearranged labdanes with aromatized B ring [J].
Philkhana, Satish Chandra ;
Reddy, D. Srinivasa .
TETRAHEDRON LETTERS, 2017, 58 (13) :1262-1264