Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance

被引:210
作者
Nicolaou, K. C. [1 ,2 ,3 ]
Hale, Christopher R. H. [1 ,2 ]
Nilewski, Christian [1 ,2 ]
Ioannidou, Heraklidia A. [1 ,2 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; STEREOCONTROLLED TOTAL-SYNTHESIS; 1ST TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; SOLID-PHASE SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; ENDIANDRIC ACID CASCADE; KEY BUILDING-BLOCKS; MARINE VERRUCOSISPORA STRAIN;
D O I
10.1039/c2cs35116a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The advent of organic synthesis and the understanding of the molecule as they occurred in the nineteenth century and were refined in the twentieth century constitute two of the most profound scientific developments of all time. These discoveries set in motion a revolution that shaped the landscape of the molecular sciences and changed the world. Organic synthesis played a major role in this revolution through its ability to construct the molecules of the living world and others like them whose primary element is carbon. Although the early beginnings of organic synthesis came about serendipitously, organic chemists quickly recognized its potential and moved decisively to advance and exploit it in myriad ways for the benefit of mankind. Indeed, from the early days of the synthesis of urea and the construction of the first carbon-carbon bond, the art of organic synthesis improved to impressively high levels of sophistication. Through its practice, today chemists can synthesize organic molecules-natural and designed-of all types of structural motifs and for all intents and purposes. The endeavor of constructing natural products-the organic molecules of nature-is justly called both a creative art and an exact science. Often called simply total synthesis, the replication of nature's molecules in the laboratory reflects and symbolizes the state of the art of synthesis in general. In the last few decades a surge in total synthesis endeavors around the world led to a remarkable collection of achievements that covers a wide ranging landscape of molecular complexity and diversity. In this article, we present highlights of some of our contributions in the field of total synthesis of natural products of biological and medicinal importance. For perspective, we also provide a listing of selected examples of additional natural products synthesized in other laboratories around the world over the last few years.
引用
收藏
页码:5185 / 5238
页数:54
相关论文
共 889 条
[1]   Novel DPPH radical scavengers, bisorbicillinol and demethyltrichodimerol, from a fungus [J].
Abe, N ;
Murata, T ;
Hirota, A .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998, 62 (04) :661-666
[2]   Novel oxidized sorbicillin dimers with 1,1-diphenyl-2-picrylhydrazyl-radical scavenging activity from a fungus [J].
Abe, N ;
Murata, T ;
Hirota, A .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998, 62 (11) :2120-2126
[3]   Total Synthesis of (+)-Scholarisine A [J].
Adams, Gregory L. ;
Carroll, Patrick J. ;
Smith, Amos B., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (09) :4037-4040
[4]   Bisanthraquinone metabolites produced by the endophytic fungus Diaporthe sp. [J].
Agusta, A ;
Ohashi, K ;
Shibuya, H .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (04) :579-582
[5]   ON THE DNA RECOGNITION ROLE OF THE CARBOHYDRATE SECTOR IN CALICHEAMICIN - A COMPARISON OF DNA-CLEAVING CAPACITY OF ENANTIOMERIC CALICHEAMICINONES [J].
AIYAR, J ;
HITCHCOCK, SA ;
DENHART, D ;
LIU, KKC ;
DANISHEFSKY, SJ ;
CROTHERS, DM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (08) :855-858
[6]   Azaspiracids modulate intracellular pH levels in human lymphocytes [J].
Alfonso, Amparo ;
Vieytes, Mercedes R. ;
Ofuji, Katsuya ;
Satake, Masayuki ;
Nicolaou, K. C. ;
Frederick, Michael O. ;
Botana, L. M. .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2006, 346 (03) :1091-1099
[7]   The chemistry and biology of epothilones - The wheel keeps turning [J].
Altmann, Karl-Heinz ;
Pfeiffer, Bernhard ;
Arseniyadis, Stellios ;
Pratt, Benjamin A. ;
Nicolaou, K. C. .
CHEMMEDCHEM, 2007, 2 (04) :396-423
[8]  
Altmann Karl-Heinz, 2009, Fortschr Chem Org Naturst, V90, P221
[9]   Natural Products as Leads for Anticancer Drug Discovery: Discovery of New Chemotypes of Microtubule Stabilizers through Reengineering of the Epothilone Scaffold [J].
Altmann, Karl-Heinz ;
Cachoux, Frederic ;
Feyen, Fabian ;
Gertsch, Juerg ;
Kuzniewski, Christian N. ;
Wartmann, Markus .
CHIMIA, 2010, 64 (1-2) :8-13
[10]   Recent developments in the chemical biology of epothilones [J].
Altmann, KH .
CURRENT PHARMACEUTICAL DESIGN, 2005, 11 (13) :1595-1613