Literature DB >> 19030533

Evolution of multi-component anion relay chemistry (ARC): construction of architecturally complex natural and unnatural products.

Amos B Smith1, William M Wuest.   

Abstract

Efficient construction of architecturally complex natural and unnatural products is the hallmark of organic chemistry. Anion relay chemistry (ARC)-a multi-component coupling protocol-has the potential to provide the chemist with a powerful synthetic tactic, enabling efficient, rapid elaboration of structurally complex scaffolds in a single operation with precise stereochemical control. The ARC tactic can be subdivided into two main classes, comprising the relay of negative charge either through bonds or through space, the latter with aid of a transfer agent. This review will present the current state of through-space anion relay, in conjunction with examples of natural and unnatural product syntheses that illustrate the utility of this synthetic method.

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Year:  2008        PMID: 19030533      PMCID: PMC2769507          DOI: 10.1039/b810394a

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


  37 in total

1.  Anion relay chemistry: an effective tactic for diversity oriented synthesis.

Authors:  Amos B Smith; Ming Xian
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

2.  Synthesis of the C11-C23 fragment of spirastrellolide A. A ketal-tethered RCM approach to the construction of spiroketals.

Authors:  Jia Liu; Richard P Hsung
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

3.  Total synthesis of the neotropical poison-frog alkaloid (-)-205B.

Authors:  Amos B Smith; Dae-Shik Kim
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

4.  Toward the total synthesis of spirastrellolide A. Part 1: Strategic considerations and preparation of the southern domain.

Authors:  Alois Fürstner; Michaël D B Fenster; Bernhard Fasching; Cédrickx Godbout; Karin Radkowski
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-18       Impact factor: 15.336

5.  Spirastrellolide B reveals the absolute configuration of the spirastrellolide macrolide core.

Authors:  Kaoru Warabi; David E Williams; Brian O Patrick; Michel Roberge; Raymond J Andersen
Journal:  J Am Chem Soc       Date:  2007-01-24       Impact factor: 15.419

6.  New acyclic sesquiterpenes and norsesquiterpenes from the Caribbean Gorgonian Plexaurella grisea.

Authors:  A Rueda; E Zubía; M J Ortega; J Salvá
Journal:  J Nat Prod       Date:  2001-04       Impact factor: 4.050

7.  Enantioselective formal total synthesis of the antitumor macrolide bryostatin 7.

Authors:  Soraya Manaviazar; Mark Frigerio; Gurpreet S Bhatia; Marc G Hummersone; Abil E Aliev; Karl J Hale
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

8.  Multigram synthesis of the C29-C51 subunit and completion of the total synthesis of altohyrtin C (spongistatin 2).

Authors:  Clayton H Heathcock; Mark McLaughlin; Jesus Medina; Jed L Hubbs; Grier A Wallace; Robert Scott; Michele M Claffey; Christopher J Hayes; Gregory R Ott
Journal:  J Am Chem Soc       Date:  2003-10-22       Impact factor: 15.419

9.  Spirastrellolide A, an antimitotic macrolide isolated from the Caribbean marine sponge Spirastrella coccinea.

Authors:  David E Williams; Michel Roberge; Rob Van Soest; Raymond J Andersen
Journal:  J Am Chem Soc       Date:  2003-05-07       Impact factor: 15.419

10.  Phase I study of bryostatin 1: assessment of interleukin 6 and tumor necrosis factor alpha induction in vivo. The Cancer Research Campaign Phase I Committee.

Authors:  P A Philip; D Rea; P Thavasu; J Carmichael; N S Stuart; H Rockett; D C Talbot; T Ganesan; G R Pettit; F Balkwill
Journal:  J Natl Cancer Inst       Date:  1993-11-17       Impact factor: 13.506

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  44 in total

1.  Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1.

Authors:  Amos B Smith; Chris Sfouggatakis; Christina A Risatti; Jeffrey B Sperry; Wenyu Zhu; Victoria A Doughty; Takashi Tomioka; Dimitar B Gotchev; Clay S Bennett; Satoshi Sakamoto; Onur Atasoylu; Shohei Shirakami; David Bauer; Makoto Takeuchi; Jyunichi Koyanagi; Yasuharu Sakamoto
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

2.  Anion relay chemistry: access to the type II ARC reaction manifold through a fundamentally different reaction pathway exploiting 1-oxa-2-silacyclopentanes and related congeners.

Authors:  Amos B Smith; Rongbiao Tong; Won-Suk Kim; William A Maio
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-10       Impact factor: 15.336

3.  Type II Anion Relay Chemistry: Conformational Constraints To Achieve Effective [1,5]-Vinyl Brook Rearrangements.

Authors:  Qi Liu; Yu Chen; Xiao Zhang; K N Houk; Yong Liang; Amos B Smith
Journal:  J Am Chem Soc       Date:  2017-06-14       Impact factor: 15.419

4.  Diversity-oriented synthesis leads to an effective class of bifunctional linchpins uniting anion relay chemistry (ARC) with benzyne reactivity.

Authors:  Amos B Smith; Won-Suk Kim
Journal:  Proc Natl Acad Sci U S A       Date:  2011-01-18       Impact factor: 11.205

5.  Seebach's conjunctive reagent enables double cyclizations.

Authors:  Brent D Chandler; Jason T Roland; Yukai Li; Erik J Sorensen
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

6.  Organic synthesis in the Smith Group: a personal selection of a dozen lessons learned at the University of Pennsylvania.

Authors:  Kevin P C Minbiole
Journal:  J Antibiot (Tokyo)       Date:  2016-03-02       Impact factor: 2.649

7.  Oxidative allene amination for the synthesis of azetidin-3-ones.

Authors:  Eileen G Burke; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-19       Impact factor: 15.336

Review 8.  The chemistry and biology of mycolactones.

Authors:  Matthias Gehringer; Karl-Heinz Altmann
Journal:  Beilstein J Org Chem       Date:  2017-08-11       Impact factor: 2.883

9.  (+)-Rimocidin synthetic studies: construction of the C(1-27) aglycone skeleton.

Authors:  Amos B Smith; Megan A Foley; Shuzhi Dong; Alia Orbin
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

10.  Validation of diethoxyphosphonate as an effective agent for charge transfer in Anion Relay Chemistry (ARC).

Authors:  Alexander Sokolsky; Amos B Smith
Journal:  Org Lett       Date:  2012-08-10       Impact factor: 6.005

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