Literature DB >> 19847336

The art of total synthesis through cascade reactions.

K C Nicolaou1, Jason S Chen.   

Abstract

The growing importance of cascade reactions reflects and imparts advances in the state of the art of organic synthesis and underscores the desire of synthetic chemists to achieve higher levels of elegance and efficiency. Besides their esthetic appeal, cascade processes offer economical and environmentally friendly means for generating molecular complexity. Because of their many advantages, these reactions have found numerous applications in the synthesis of complex molecules, both natural and designed. In this tutorial review, we highlight the design and execution of cascade reactions within the context of total synthesis as demonstrated with selected examples from these laboratories.

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Year:  2009        PMID: 19847336      PMCID: PMC2766600          DOI: 10.1039/b903290h

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


  20 in total

Review 1.  Cascade reactions in total synthesis.

Authors:  K C Nicolaou; David J Edmonds; Paul G Bulger
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-06       Impact factor: 15.336

2.  Total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin.

Authors:  K C Nicolaou; Yee Hwee Lim; Jared L Piper; Charles D Papageorgiou
Journal:  J Am Chem Soc       Date:  2007-03-14       Impact factor: 15.419

Review 3.  From amino acids to heteroaromatics--thiopeptide antibiotics, nature's heterocyclic peptides.

Authors:  Rachael A Hughes; Christopher J Moody
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Bisanthraquinone metabolites produced by the endophytic fungus Diaporthe sp.

Authors:  Andria Agusta; Kazuyoshi Ohashi; Hirotaka Shibuya
Journal:  Chem Pharm Bull (Tokyo)       Date:  2006-04       Impact factor: 1.645

5.  Biyouyanagin A, an anti-HIV agent from Hypericum chinense L. var. salicifolium.

Authors:  Naonobu Tanaka; Mamoru Okasaka; Youko Ishimaru; Yoshihisa Takaishi; Mitsunobu Sato; Masato Okamoto; Tetsuya Oshikawa; Sharif Uddin Ahmed; L Mark Consentino; Kuo-Hsiung Lee
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

6.  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

7.  Total synthesis of thiostrepton. Retrosynthetic analysis and construction of key building blocks.

Authors:  K C Nicolaou; Brian S Safina; Mark Zak; Sang Hyup Lee; Marta Nevalainen; Marco Bella; Anthony A Estrada; Christian Funke; Frédéric J Zécri; Stephan Bulat
Journal:  J Am Chem Soc       Date:  2005-08-10       Impact factor: 15.419

8.  2,2'-dimethoxy-4a,4a'-dehydrorugulosin (rugulin), a minor metabolite from Penicillium rugulosum.

Authors:  P Sedmera; M Podojil; J Vokoun; V Betina; P Nemec
Journal:  Folia Microbiol (Praha)       Date:  1978       Impact factor: 2.099

9.  Total synthesis, revised structure, and biological evaluation of biyouyanagin A and analogues thereof.

Authors:  K C Nicolaou; T Robert Wu; David Sarlah; David M Shaw; Eric Rowcliffe; Dennis R Burton
Journal:  J Am Chem Soc       Date:  2008-07-23       Impact factor: 15.419

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  67 in total

1.  REGIOSELECTIVE MULTICOMPONENT DOMINO REACTIONS PROVIDING RAPID AND EFFICIENT ROUTES TO FUSED ACRIDINES.

Authors:  Jin-Peng Zhang; Wei Fan; Jie Ding; Bo Jiang; Shu-Jiang Tu; Guigen Li
Journal:  Heterocycles       Date:  2013-12-17       Impact factor: 0.831

2.  Natural product-inspired cascade synthesis yields modulators of centrosome integrity.

Authors:  Heiko Dückert; Verena Pries; Vivek Khedkar; Sascha Menninger; Hanna Bruss; Alexander W Bird; Zoltan Maliga; Andreas Brockmeyer; Petra Janning; Anthony Hyman; Stefan Grimme; Markus Schürmann; Hans Preut; Katja Hübel; Slava Ziegler; Kamal Kumar; Herbert Waldmann
Journal:  Nat Chem Biol       Date:  2011-12-25       Impact factor: 15.040

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.  Organocatalytic cascade reactions as a new tool in total synthesis.

Authors:  Christoph Grondal; Matthieu Jeanty; Dieter Enders
Journal:  Nat Chem       Date:  2010-02-19       Impact factor: 24.427

5.  Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.

Authors:  Alan Rolfe; Thiwanka B Samarakoon; Paul R Hanson
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

6.  S(N)Ar-based, facile synthesis of a library of benzothiaoxazepine-1,1'-dioxides.

Authors:  Alan Rolfe; Thiwanka B Samarakoon; Sarra V Klimberg; Marek Brzozowski; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson
Journal:  J Comb Chem       Date:  2010-09-29

Review 7.  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

Review 8.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

Review 9.  Opportunities of Covalent Organic Frameworks for Advanced Applications.

Authors:  Yanpei Song; Qi Sun; Briana Aguila; Shengqian Ma
Journal:  Adv Sci (Weinh)       Date:  2018-11-12       Impact factor: 16.806

Review 10.  Enzymatic Cascade Reactions in Biosynthesis.

Authors:  Christopher T Walsh; Bradley S Moore
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-20       Impact factor: 15.336

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