Literature DB >> 22743704

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

K C Nicolaou1, Christopher R H Hale, Christian Nilewski, Heraklidia A Ioannidou.   

Abstract

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.

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Year:  2012        PMID: 22743704      PMCID: PMC3426871          DOI: 10.1039/c2cs35116a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  511 in total

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Authors:  K C Nicolaou; Paraselli Bheema Rao; Junliang Hao; Mali Venkat Reddy; Gerasimos Rassias; Xianhai Huang; David Y-K Chen; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-17       Impact factor: 15.336

2.  Total synthesis of halichondrin C.

Authors:  Akihiko Yamamoto; Atsushi Ueda; Paul Brémond; Paolo S Tiseni; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2011-12-23       Impact factor: 15.419

3.  Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A.

Authors:  Michael T Crimmins; J Lucas Zuccarello; Pamela A Cleary; Jonathan D Parrish
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

4.  Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp.

Authors:  J W Kim; H Adachi; K Shin-ya; Y Hayakawa; H Seto
Journal:  J Antibiot (Tokyo)       Date:  1997-07       Impact factor: 2.649

5.  Probing the role of the mycosamine C2'-OH on the activity of amphotericin B.

Authors:  Mitchell P Croatt; Erick M Carreira
Journal:  Org Lett       Date:  2011-02-15       Impact factor: 6.005

6.  Diastereoselective total synthesis of (±)-schindilactone A.

Authors:  Qing Xiao; Wei-Wu Ren; Zhi-Xing Chen; Tian-Wen Sun; Yong Li; Qin-Da Ye; Jian-Xian Gong; Fan-Ke Meng; Lin You; Yi-Fan Liu; Ming-Zhe Zhao; Ling-Min Xu; Zhen-Hua Shan; Ying Shi; Ye-Feng Tang; Jia-Hua Chen; Zhen Yang
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-07       Impact factor: 15.336

7.  Total synthesis and absolute stereochemical assignment of kibdelone C.

Authors:  David L Sloman; Jeffrey W Bacon; John A Porco
Journal:  J Am Chem Soc       Date:  2011-06-15       Impact factor: 15.419

8.  Chemistry, Biology, and Medicine of the Glycopeptide Antibiotics.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

9.  From nature to the laboratory and into the clinic.

Authors:  K C Nicolaou; Jason S Chen; Stephen M Dalby
Journal:  Bioorg Med Chem       Date:  2008-11-06       Impact factor: 3.641

10.  Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis.

Authors:  David A Evans; Lisbet Kvaernø; Travis B Dunn; André Beauchemin; Brian Raymer; Jason A Mulder; Edward J Olhava; Martin Juhl; Katsuji Kagechika; David A Favor
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

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  23 in total

1.  Synthesis of deoxyelephantopin analogues.

Authors:  Roman Lagoutte; Christelle Serba; Nicolas Winssinger
Journal:  J Antibiot (Tokyo)       Date:  2017-11-01       Impact factor: 2.649

Review 2.  Marine Mollusk-Derived Agents with Antiproliferative Activity as Promising Anticancer Agents to Overcome Chemotherapy Resistance.

Authors:  Maria Letizia Ciavatta; Florence Lefranc; Marianna Carbone; Ernesto Mollo; Margherita Gavagnin; Tania Betancourt; Ramesh Dasari; Alexander Kornienko; Robert Kiss
Journal:  Med Res Rev       Date:  2016-12-07       Impact factor: 12.944

3.  Medicinal Chemistry Profiling of Monocyclic 1,2-Azaborines.

Authors:  Peng Zhao; David O Nettleton; Rajeshri G Karki; Frédéric J Zécri; Shih-Yuan Liu
Journal:  ChemMedChem       Date:  2017-02-21       Impact factor: 3.466

Review 4.  How thiostrepton was made in the laboratory.

Authors:  K C Nicolaou
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-03       Impact factor: 15.336

5.  Rescuing auxotrophic microorganisms with nonenzymatic chemistry.

Authors:  Yunmi Lee; Afoma Umeano; Emily P Balskus
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-20       Impact factor: 15.336

Review 6.  Organic synthesis: the art and science of replicating the molecules of living nature and creating others like them in the laboratory.

Authors:  K C Nicolaou
Journal:  Proc Math Phys Eng Sci       Date:  2014-03-08       Impact factor: 2.704

7.  Studies Targeting Ryanodol Result in an Annulation Reaction for the Synthesis of a Variety of Fused Carbocycles.

Authors:  Rajdip Karmakar; Arnold L Rheingold; Glenn C Micalizio
Journal:  Org Lett       Date:  2019-07-12       Impact factor: 6.005

8.  One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates.

Authors:  D Jamin Keith; Stefan A Marasligiller; Alexander W Sasse; Steven D Townsend
Journal:  J Vis Exp       Date:  2018-01-15       Impact factor: 1.355

Review 9.  The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

Authors:  Melanie Trobe; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

Review 10.  Opportunities for merging chemical and biological synthesis.

Authors:  Stephen Wallace; Emily P Balskus
Journal:  Curr Opin Biotechnol       Date:  2014-04-18       Impact factor: 9.740

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