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

页码：5383 / 5394

页数：12

共 55 条

[1] Biogenesis-Inspired, Divergent Synthesis of Spirochensilide A, Spirochensilide B, and Abifarine B Employing a Radical-Polar Crossover [J].

Alekseychuk, Mykhaylo ;

Adrian, Sinan ;

Heinze, Robert C. ;

Heretsch, Philipp .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (26) :11574-11579

[2] Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products [J].

Brill, Zachary G. ;

Condakes, Matthew L. ;

Ting, Chi P. ;

Maimone, Thomas J. .

CHEMICAL REVIEWS, 2017, 117 (18) :11753-11795

[3] The Combined C-H Functionalization/Cope Rearrangement: Discovery and Applications in Organic Synthesis [J].

Davies, Huw M. L. ;

Lian, Yajing .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :923-935

[4] Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step [J].

Delayre, Bastien ;

Wang, Qian ;

Zhu, Jieping .

ACS CENTRAL SCIENCE, 2021, 7 (04) :559-569

[5] Rapid access to the "in,out"-tetracyclic core of ingenol" [J].

Epstein, OL ;

Cha, JK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :121-123

[6] Total Synthesis of (+)-Alsmaphorazine C and Formal Synthesis of (+)-Strictamine: A Photo-Fries Approach [J].

Gao, Beiling ;

Yao, Fengjie ;

Zhang, Zhaodong ;

Ding, Hanfeng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (19) :10603-10607

[7] Tetracyclic Diterpenoid Synthesis Facilitated by ODI-Cascade Approaches to Bicyclo[3.2.1]octane Skeletons [J].

Gao, Kai ;

Hu, Jialei ;

Ding, Hanfeng .

ACCOUNTS OF CHEMICAL RESEARCH, 2021, 54 (04) :875-889

[8]

Guo L., 2022, ANGEW CHEM, V61

[9] Tailored Synthesis of Skeletally Diverse Stemona Alkaloids through Chemoselective Dyotropic Rearrangements of β-Lactones [J].

Guo, Zhen ;

Bao, Ruiyang ;

Li, Yuanhe ;

Li, Yunshan ;

Zhang, Jingyang ;

Tang, Yefeng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (26) :14545-14553

[10] Total Syntheses of Highly Oxidized ent-Kaurenoids Pharicin A, Pharicinin B, 7-O-Acetylpseurata C, and Pseurata C: A [5+2] Cascade Approach [J].

He, Chi ;

Hu, Jialei ;

Wu, Yubing ;

Ding, Hanfeng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (17) :6098-6101

← 1 2 3 4 5 6 →