Bioinspired Total Synthesis of Polycyclic Natural Products

被引:0
作者
Ishikawa, Hayato [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, 1-8-1 Inohana,Chuo Ku, Chiba 2608675, Japan
关键词
total synthesis; indole alkaloid; iridoid glycoside; bioinspired reaction; collective synthesis; ALKALOIDS; STRICTOSIDINE; DERIVATIVES; SYNTHASE;
D O I
10.1248/cpb.c24-00843
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Despite the great strides in biopharmaceuticals and monoclonal antibodies today, natural products remain highly attractive as drug candidates. Therefore, building a library of natural products through total synthesis is critically important for drug discovery. This perspective article details the collective total synthesis of polycyclic natural products using "bioinspired reactions" that mimic natural product biosynthesis. It discusses the total syntheses of 20 natural products, including dimeric diketopiperazine alkaloids, monoterpenoid indole alkaloids, and iridoid glycosides, each achieved in fewer than 14 steps starting from commercially available materials.
引用
收藏
页码:67 / 77
页数:11
相关论文
共 41 条
[1]  
AIMI N, 1986, CHEM PHARM BULL, V34, P3064
[2]  
Anthoni U, 1999, ALKAL CHEM, V13, P163, DOI 10.1016/S0735-8210(99)80025-9
[3]   Total Synthesis of (-)-Strictosidine and Interception of Aryne Natural Product Derivatives "Strictosidyne" and "Strictosamidyne" [J].
Anthony, Sarah M. ;
Tona, Veronica ;
Zou, Yike ;
Morrill, Lucas A. ;
Billingsley, John M. ;
Lim, Megan ;
Tang, Yi ;
Houk, K. N. ;
Garg, Neil K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (19) :7471-7479
[4]   IRIDOIDS - AN UPDATED REVIEW .2. [J].
BOROS, CA ;
STERMITZ, FR .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (05) :1173-1246
[5]   IRIDOIDS - AN UPDATED REVIEW .1. [J].
BOROS, CA ;
STERMITZ, FR .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (05) :1055-1147
[6]   REARRANGEMENT OF CATHARANTHINE, STEMMADENINE, AND TABERSONINE IN ACETIC ACID [J].
BROWN, RT ;
HILL, JS ;
SMITH, GF ;
STAPLEFO.KS ;
POISSON, J ;
MUQUET, M ;
KUNESCH, N .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (24) :1475-&
[7]   Strictosidine Synthase Triggered Enantioselective Synthesis of N-Substituted (S)-3,14,18,19-Tetrahydroangustines as Novel Topoisomerase I Inhibitors [J].
Cai, Yunrui ;
Zhu, Huajian ;
Alperstein, Zaccary ;
Yu, Wenjun ;
Cherkasov, Artem ;
Zou, Hongbin .
ACS CHEMICAL BIOLOGY, 2017, 12 (12) :3086-3092
[8]  
Cordell G.A., 1981, In Introduction to Alkaloids. A Biogenetic Approach, DOI 10.1002/jps.2600720334
[9]   Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative [J].
Dou, Yingchao ;
Kouklovsky, Cyrille ;
Gandon, Vincent ;
Vincent, Guillaume .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (04) :1527-1531
[10]   FACILE REDUCTION OF ETHYL THIOL ESTERS TO ALDEHYDES - APPLICATION TO A TOTAL SYNTHESIS OF (+)-NEOTHRAMYCIN-A METHYL-ETHER [J].
FUKUYAMA, T ;
LIN, SC ;
LI, LP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7050-7051