Literature DB >> 12669826

Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis.

K C Nicolaou1, Tamsyn Montagnon, Scott A Snyder.   

Abstract

Cascade reactions and biomimetic strategies are being increasingly applied to the construction of natural and designed molecules. Such processes, in which ideally a single event triggers the conversion of a starting material to a product which then becomes a substrate for the next reaction until termination leads to a stable final product, are highly desirable not only due to their elegance, but also because of their efficiency and economy in terms of reagent consumption and purification. Often, these multistep, one-pot procedures are accompanied by dramatic increases in molecular complexity and impressive selectivity. The discovery of new molecular diversity from Nature and the demand for more efficient and environmentally benign chemical processes dictates and invites the further development of such synthetic strategies and tactics as we move into a new age of chemical synthesis. Within this article, a number of instructive examples of such synthetic strategies from the principal author's laboratories are discussed.

Mesh:

Year:  2003        PMID: 12669826     DOI: 10.1039/b209440c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  47 in total

1.  Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents.

Authors:  Venukrishnan Komanduri; Fernando Pedraza; Michael J Krische
Journal:  Adv Synth Catal       Date:  2008-07-07       Impact factor: 5.837

Review 2.  The essence of total synthesis.

Authors:  K C Nicolaou; Scott A Snyder
Journal:  Proc Natl Acad Sci U S A       Date:  2004-08-09       Impact factor: 11.205

Review 3.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

Review 4.  Total (bio)synthesis: strategies of nature and of chemists.

Authors:  Alexandra A Roberts; Katherine S Ryan; Bradley S Moore; Tobias A M Gulder
Journal:  Top Curr Chem       Date:  2010

5.  Total synthesis of atrochamins F, H, I, and J through cascade reactions.

Authors:  K C Nicolaou; Troy Lister; Ross M Denton; Christine F Gelin
Journal:  Tetrahedron       Date:  2008-05-19       Impact factor: 2.457

6.  Diastereoselective, three-component cascade synthesis of tetrahydrofurans and tetrahydropyrans employing the tandem Mukaiyama aldol-lactonization process.

Authors:  T Andrew Mitchell; Cunxiang Zhao; Daniel Romo
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

7.  Four-component domino reaction providing an easy access to multifunctionalized tricyclo[6.2.2.0(1,6)]dodecane derivatives.

Authors:  Bo Jiang; Chao Li; Feng Shi; Shu-Jiang Tu; Parminder Kaur; Walter Wever; Guigen Li
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

8.  Total synthesis and absolute configuration of the bisanthraquinone antibiotic BE-43472B.

Authors:  K C Nicolaou; Yee Hwee Lim; Jochen Becker
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Total synthesis and biological evaluation of (+)- and (-)-bisanthraquinone antibiotic BE-43472B and related compounds.

Authors:  K C Nicolaou; Jochen Becker; Yee Hwee Lim; Alexandre Lemire; Thomas Neubauer; Ana Montero
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

10.  8H-Chromeno[2',3':4,5]imidazo[2,1-a]isoquinoline.

Authors:  Saifidin Safarov; Leonid G Voskressensky; Oksana V Bizhko; Larisa N Kulikova; Victor N Khrustalev
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-02-27
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