Literature DB >> 19152273

Inspirations, discoveries, and future perspectives in total synthesis.

K C Nicolaou1.   

Abstract

The last one hundred years have witnessed a dramatic increase in the power and reach of total synthesis. The pantheon of accomplishments in the field includes the total synthesis of molecules of unimaginable beauty and diversity such as the four discussed in this article: endiandric acids (1982), calicheamicin gamma(1)(I) (1992), Taxol (1994), and brevetoxin B (1995). Chosen from the collection of the molecules synthesized in the author's laboratories, these structures are but a small fraction of the myriad constructed in laboratories around the world over the last century. Their stories, and the background on which they were based, should serve to trace the evolution of the art of chemical synthesis to its present sharp condition, an emergence that occurred as a result of new theories and mechanistic insights, new reactions, new reagents and catalysts, and new synthetic technologies and strategies. Indeed, the advent of chemical synthesis as a whole must be considered as one of the most influential developments of the twentieth century in terms of its impact on society.

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Year:  2009        PMID: 19152273      PMCID: PMC2672623          DOI: 10.1021/jo802351b

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  123 in total

1.  Total synthesis of colombiasin A and determination of its absolute configuration.

Authors:  K C Nicolaou; G Vassilikogiannakis; W Mägerlein; R Kranich
Journal:  Chemistry       Date:  2001-12-17       Impact factor: 5.236

2.  Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 3. Completion and synthesis of advanced analogues.

Authors:  K C Nicolaou; Y-L Zhong; P S Baran; J Jung; H-S Choi; W H Yoon
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

3.  The second total synthesis of diazonamide A.

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

4.  Total synthesis of the proposed azaspiracid-1 structure, part 1: construction of the enantiomerically pure C1-C20, C21-C27, and C28-C40 fragments.

Authors:  K C Nicolaou; Yiwei Li; Noriaki Uesaka; Theocharis V Koftis; Stepan Vyskocil; Taotao Ling; Mugesh Govindasamy; Wenyuan Qian; Federico Bernal; David Y-K Chen
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-11       Impact factor: 15.336

5.  Total synthesis and structural elucidation of azaspiracid-1. Synthesis-based analysis of originally proposed structures and indication of their non-identity to the natural product.

Authors:  K C Nicolaou; David Y-K Chen; Yiwei Li; Noriaki Uesaka; Goran Petrovic; Theocharis V Koftis; Federico Bernal; Michael O Frederick; Mugesh Govindasamy; Taotao Ling; Petri M Pihko; Wenjun Tang; Stepan Vyskocil
Journal:  J Am Chem Soc       Date:  2006-02-22       Impact factor: 15.419

6.  On the structure of maitotoxin.

Authors:  K C Nicolaou; Michael O Frederick
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  Total synthesis of (-)-gambierol.

Authors:  Haruhiko Fuwa; Noriko Kainuma; Kazuo Tachibana; Makoto Sasaki
Journal:  J Am Chem Soc       Date:  2002-12-18       Impact factor: 15.419

Review 8.  Chemistry and biology of natural and designed enediynes.

Authors:  K C Nicolaou; A L Smith; E W Yue
Journal:  Proc Natl Acad Sci U S A       Date:  1993-07-01       Impact factor: 11.205

9.  Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 1. Racemic and asymmetric synthesis of bicyclo[4.3.1] key building blocks.

Authors:  K C Nicolaou; J Jung; W H Yoon; K C Fong; H-S Choi; Y He; Y-L Zhong; P S Baran
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

10.  Taxol stabilizes microtubules in mouse fibroblast cells.

Authors:  P B Schiff; S B Horwitz
Journal:  Proc Natl Acad Sci U S A       Date:  1980-03       Impact factor: 11.205

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  4 in total

Review 1.  Is there no end to the total syntheses of strychnine? Lessons learned in strategy and tactics in total synthesis.

Authors:  Jeffrey S Cannon; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-19       Impact factor: 15.336

2.  Phenylisoserine in the gas-phase and water: Ab initio studies on neutral and zwitterion conformers.

Authors:  Joanna E Rode; Jan Cz Dobrowolski; Joanna Sadlej
Journal:  J Mol Model       Date:  2010-07-11       Impact factor: 1.810

Review 3.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

4.  Competition-driven selection in covalent dynamic networks and implementation in organic reactional selectivity.

Authors:  P Kovaříček; A C Meister; K Flídrová; R Cabot; K Kovaříčková; J-M Lehn
Journal:  Chem Sci       Date:  2016-02-10       Impact factor: 9.825

  4 in total

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