Literature DB >> 18266375

Enantioselective synthesis of bicyclo[2.2.2]octenones using a copper-mediated oxidative dearomatization/[4 + 2] dimerization cascade.

Suwei Dong1, Jianglong Zhu, John A Porco.   

Abstract

An enantioselective approach to bicyclo[2.2.2]octenone structures utilizing a copper-mediated asymmetric oxidative dearomatization/[4 + 2] dimerization cascade is described. The total synthesis and absolute stereochemistry reassignment of (+)-aquaticol has been achieved using the methodology.

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Year:  2008        PMID： 18266375      PMCID： PMC2660372          DOI： 10.1021/ja711018z

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  12 in total

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Authors:  S Itoh; H Kumei; M Taki; S Nagatomo; T Kitagawa; S Fukuzumi
Journal:  J Am Chem Soc       Date:  2001-07-11       Impact factor: 15.419

Review 2.  Structure and spectroscopy of copper-dioxygen complexes.

Authors:  Liviu M Mirica; Xavier Ottenwaelder; T Daniel P Stack
Journal:  Chem Rev       Date:  2004-02       Impact factor: 60.622

3.  Progress toward the total synthesis of bacchopetiolone: application of a tandem aromatic oxidation/Diels-Alder reaction.

Authors:  Amélie Bérubé; Ioana Drutu; John L Wood
Journal:  Org Lett       Date:  2006-11-23       Impact factor: 6.005

4.  Aliphatic Hydroxylation by a Bis(µ-oxo)dicopper(III) Complex.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-01       Impact factor: 15.336

5.  Tyrosinase reactivity in a model complex: an alternative hydroxylation mechanism.

Authors:  Liviu M Mirica; Michael Vance; Deanne Jackson Rudd; Britt Hedman; Keith O Hodgson; Edward I Solomon; T Daniel P Stack
Journal:  Science       Date:  2005-06-24       Impact factor: 47.728

6.  Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization.

Authors:  Jianglong Zhu; Nicholas P Grigoriadis; Jonathan P Lee; John A Porco
Journal:  J Am Chem Soc       Date:  2005-07-06       Impact factor: 15.419

7.  Reversible O-O bond cleavage in copper-dioxygen isomers: impact of anion basicity.

Authors:  Xavier Ottenwaelder; Deanne Jackson Rudd; Mary C Corbett; Keith O Hodgson; Britt Hedman; T Daniel P Stack
Journal:  J Am Chem Soc       Date:  2006-07-26       Impact factor: 15.419

Review 8.  Oxidant types in copper-dioxygen chemistry: the ligand coordination defines the Cu(n)-O2 structure and subsequent reactivity.

Authors:  Lanying Q Hatcher; Kenneth D Karlin
Journal:  J Biol Inorg Chem       Date:  2004-08-10       Impact factor: 3.358

9.  mu-eta2:eta2-peroxodicopper(II) complex with a secondary diamine ligand: a functional model of tyrosinase.

Authors:  Liviu M Mirica; Deanne Jackson Rudd; Michael A Vance; Edward I Solomon; Keith O Hodgson; Britt Hedman; T Daniel P Stack
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

10.  Reversible cleavage and formation of the dioxygen O-O bond within a dicopper complex.

Authors:  J A Halfen; S Mahapatra; E C Wilkinson; S Kaderli; V G Young; L Que; A D Zuberbühler; W B Tolman
Journal:  Science       Date:  1996-03-08       Impact factor: 47.728
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  21 in total

1.  Microwave-based reaction screening: tandem retro-Diels-Alder/Diels-Alder cycloadditions of o-quinol dimers.

Authors:  Suwei Dong; Katharine J Cahill; Moon-Il Kang; Nancy H Colburn; Curtis J Henrich; Jennifer A Wilson; John A Beutler; Richard P Johnson; John A Porco
Journal:  J Org Chem       Date:  2011-10-07       Impact factor: 4.354

Review 2.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

3.  Controlling the facial selectivity of asymmetric [4+2] cyclo-additions: a concise synthesis of the cis-decalin core structure of superstolides A and B.

Authors:  Lei Chen; Zhengmao Hua; Gangqin Li; Zhendong Jin
Journal:  Org Lett       Date:  2011-06-14       Impact factor: 6.005

4.  Arenophile-Mediated Dearomative Reduction.

Authors:  Mikiko Okumura; Stephanie M Nakamata Huynh; Jola Pospech; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-23       Impact factor: 15.336

5.  Enantioselective Phenolic α-Oxidation Using H2O2 via an Unusual Double Dearomatization Mechanism.

Authors:  Michael F McLaughlin; Elisabetta Massolo; Shubin Liu; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2019-01-30       Impact factor: 15.419

6.  Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K.

Authors:  Ji Qi; Aaron B Beeler; Qiang Zhang; John A Porco
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

Review 7.  Chemoenzymatic Total Synthesis of Natural Products.

Authors:  Suman Chakrabarty; Evan O Romero; Joshua B Pyser; Jessica A Yazarians; Alison R H Narayan
Journal:  Acc Chem Res       Date:  2021-02-18       Impact factor: 22.384

8.  Photocatalytic Oxidative Dearomatization of Orcinaldehyde Derivatives.

Authors:  Summer A Baker Dockrey; Alison R H Narayan
Journal:  Org Lett       Date:  2020-04-15       Impact factor: 6.005

9.  Asymmetric oxidation of o-alkylphenols with chiral 2-(o-iodoxyphenyl)-oxazolines.

Authors:  Jagadish K Boppisetti; Vladimir B Birman
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

10.  Enantioselective synthesis of (+)-chamaecypanone C: a novel microtubule inhibitor.

Authors:  Suwei Dong; Ernest Hamel; Ruoli Bai; David G Covell; John A Beutler; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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