Literature DB >> 19415907

Manganese(III)-mediated transformations of phloroglucinols: a formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones.

Branko Mitasev1, John A Porco.   

Abstract

Manganese(III)-mediated oxidative transformations of dearomatized phloroglucinol (1,3,5-trihydroxybenzene) derivatives are reported. A number of cyclization modes have been observed, including polycyclization to afford bicyclo[2.2.2]octadiones via a formal oxidative radical [4 + 2] cycloaddition.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19415907      PMCID： PMC2740479          DOI： 10.1021/ol900590t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  Manganese(III)-Based Oxidative Free-Radical Cyclizations.

Authors:  Barry B. Snider
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Mechanistic implications of the stereochemistry of the cation radical diels-alder cycloaddition of 4-(cis-2-Deuteriovinyl)anisole to 1,3-cyclopentadiene

Authors: 
Journal:  J Org Chem       Date:  2000-09-22       Impact factor: 4.354

3.  New phloroglucinol derivatives from Hypericum papuanum.

Authors:  K Winkelmann; J Heilmann; O Zerbe; T Rali; O Sticher
Journal:  J Nat Prod       Date:  2000-01       Impact factor: 4.050

4.  Intermolecular oxidative enolate heterocoupling.

Authors:  Phil S Baran; Michael P DeMartino
Journal:  Angew Chem Int Ed Engl       Date:  2006-10-27       Impact factor: 15.336

5.  Mn(III)-Based Oxidative Free-Radical Cyclizations of Unsaturated Ketones.

Authors:  Bridget McCarthy Cole; Luning Han; Barry B. Snider
Journal:  J Org Chem       Date:  1996-11-01       Impact factor: 4.354

6.  Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: total synthesis of (+/-)-clusianone(1).

Authors:  Ji Qi; John A Porco
Journal:  J Am Chem Soc       Date:  2007-09-29       Impact factor: 15.419

7.  Nemorosone, the major constituent of floral resins of Clusia rosea.

Authors:  O Cuesta-Rubio; H Velez-Castro; B A Frontana-Uribe; J Cardenas
Journal:  Phytochemistry       Date:  2001-05       Impact factor: 4.072

8.  Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3,4,5,6- hexahydro-1,5-methano-3-benzazocine.

Authors:  Crystal G Bashore; Michael G Vetelino; Michael C Wirtz; Paige R Brooks; Heather N Frost; Ruth E McDermott; David C Whritenour; John A Ragan; Jennifer L Rutherford; Teresa W Makowski; Steven J Brenek; Jotham W Coe
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

9.  Intermolecular enolate heterocoupling: scope, mechanism, and application.

Authors:  Michael P DeMartino; Ke Chen; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-08-05       Impact factor: 15.419

10.  Total synthesis of hybocarpone and analogues thereof. A facile dimerization of naphthazarins to pentacyclic systems.

Authors:  K C Nicolaou; David L F Gray
Journal:  J Am Chem Soc       Date:  2004-01-21       Impact factor: 15.419
View more
  11 in total

1.  Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Authors:  Mikayo Hayashi; Lauren E Brown; John A Porco
Journal:  European J Org Chem       Date:  2016-10

2.  Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.

Authors:  Zachary Powers; Adam Scharf; Andrea Cheng; Feng Yang; Martin Himmelbauer; Takaaki Mitsuhashi; Lena Barra; Yoshimasa Taniguchi; Takashi Kikuchi; Makoto Fujita; Ikuro Abe; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-25       Impact factor: 15.336

3.  Total synthesis of plukenetione A.

Authors:  Qiang Zhang; Branko Mitasev; Ji Qi; John A Porco
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

Review 4.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

5.  Total Synthesis and Anticancer Activity of (+)-Hypercalin C and Congeners.

Authors:  Yongfeng Tao; Keighley Reisenauer; Joseph H Taube; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-01       Impact factor: 15.336

6.  Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization.

Authors:  Jonathan H Boyce; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

7.  Synthetic Efforts Toward [3.3.1] Bridged Bicyclic Phloroglucinol Natural Products.

Authors:  Jon T Njardarson
Journal:  Tetrahedron       Date:  2011-10-07       Impact factor: 2.457

Review 8.  An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors:  Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal:  Nat Prod Rep       Date:  2020-09-15       Impact factor: 13.423

9.  Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.

Authors:  Alexander J Grenning; Jonathan H Boyce; John A Porco
Journal:  J Am Chem Soc       Date:  2014-08-07       Impact factor: 15.419

10.  Synthesis and Multiplexed Activity Profiling of Synthetic Acylphloroglucinol Scaffolds.

Authors:  Jonathan H Boyce; Benjamin J Reisman; Brian O Bachmann; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-30       Impact factor: 15.336
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.