Literature DB >> 28082832

Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Mikayo Hayashi1, Lauren E Brown2, John A Porco3.   

Abstract

Enantioenriched, polycyclic compounds were obtained from a simple acylphloroglucinol scaffold. Highly enantioselective dearomatization was accomplished using a Trost ligand-palladium(0) complex. A computational DFT model was developed to rationalize observed enantioselectivities and revealed a key reactant-ligand hydrogen bonding interaction. Dearomatized products were used in visible light-mediated photocycloadditions and oxidative free radical cyclizations to obtain novel polycyclic chemotypes including tricyclo[4.3.1.01,4]decan-10-ones, bicyclo[3.2.1]octan-8-ones and highly-substituted cycloheptanones.

Entities:  

Keywords:  asymmetric catalysis; dearomatization; photocatalysis; polycycles; radical reactions

Year:  2016        PMID： 28082832      PMCID： PMC5222469          DOI： 10.1002/ejoc.201601003

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  28 in total

Review 1.  Target-oriented and diversity-oriented organic synthesis in drug discovery.

Authors:  S L Schreiber
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

2.  Biomimetic synthesis of polycyclic polyprenylated acylphloroglucinol natural products isolated from Hypericum papuanum.

Authors:  Jonathan H George; Micha D Hesse; Jack E Baldwin; Robert M Adlington
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

3.  Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model.

Authors:  Barry M Trost; Michelle R Machacek; Aaron Aponick
Journal:  Acc Chem Res       Date:  2006-10       Impact factor: 22.384

4.  [2+2] cycloaddition of 1,3-dienes by visible light photocatalysis.

Authors:  Anna E Hurtley; Zhan Lu; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-01       Impact factor: 15.336

5.  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

6.  Catalytic Alkene Carboaminations Enabled by Oxidative Proton-Coupled Electron Transfer.

Authors:  Gilbert J Choi; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2015-07-15       Impact factor: 15.419

7.  Progress toward the Synthesis of garsubellin A and related phloroglucins: the direct diastereoselective synthesis of the bicyclo[3.3.1]nonane core.

Authors:  Sarah J Spessard; Brian M Stoltz
Journal:  Org Lett       Date:  2002-05-30       Impact factor: 6.005

8.  Visible light photocatalysis of [2+2] styrene cycloadditions by energy transfer.

Authors:  Zhan Lu; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-10       Impact factor: 15.336

9.  Structure-based rationale for selectivity in the asymmetric allylic alkylation of cycloalkenyl esters employing the Trost 'Standard Ligand' (TSL): isolation, analysis and alkylation of the monomeric form of the cationic eta(3)-cyclohexenyl complex [(eta(3)-c-C6H9)Pd(TSL)]+.

Authors:  Craig P Butts; Emane Filali; Guy C Lloyd-Jones; Per-Ola Norrby; David A Sale; York Schramm
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

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

Authors:  Branko Mitasev; John A Porco
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005
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  2 in total

1.  Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-epi-Garcimultiflorone A.

Authors:  Saishuai Wen; Jonathan H Boyce; Sunil K Kandappa; Jayaraman Sivaguru; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-02       Impact factor: 15.419

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
  2 in total

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