Literature DB >> 22804454

Enantioselective photocycloaddition of 3-hydroxyflavones: total syntheses and absolute configuration assignments of (+)-ponapensin and (+)-elliptifoline.

Neil J Lajkiewicz1, Stéphane P Roche, Baudouin Gerard, John A Porco.   

Abstract

We have previously reported development of biomimetic, asymmetric [3 + 2] photocycloadditions between 3-hydroxyflavones and cinnamate dipolarophiles to access (-)-rocaglamide and related natural products. Herein, we describe enantioselective syntheses of aglain cycloadducts leading to the first total syntheses and absolute configuration assignments of the aglain natural products (+)-ponapensin and (+)-elliptifoline.

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Year:  2012        PMID： 22804454      PMCID： PMC3529213          DOI： 10.1021/ja305342f

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


  34 in total

1.  Cytotoxic constituents from leaves of Aglaia elliptifolia.

Authors:  S K Wang; Y J Cheng; C Y Duh
Journal:  J Nat Prod       Date:  2001-01       Impact factor: 4.050

2.  Absolute structure and absolute configuration.

Authors: 
Journal:  Acta Crystallogr A       Date:  1999-09-01       Impact factor: 2.290

3.  Parallel kinetic resolution of racemic mixtures: a new strategy for the preparation of enantiopure compounds?

Authors:  Juan R Dehli; Vicente Gotor
Journal:  Chem Soc Rev       Date:  2002-11       Impact factor: 54.564

4.  Toward ideal (trans)esterification by use of fluorous distannoxane catalysts.

Authors:  Junzo Otera
Journal:  Acc Chem Res       Date:  2004-05       Impact factor: 22.384

5.  Catalytic transamidation under moderate conditions.

Authors:  Sarah E Eldred; David A Stone; Samuel H Gellman; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419

6.  Catalytic ester-amide exchange using group (IV) metal alkoxide-activator complexes.

Authors:  Chong Han; Jonathan P Lee; Emil Lobkovsky; John A Porco
Journal:  J Am Chem Soc       Date:  2005-07-20       Impact factor: 15.419

7.  Diamide derivatives and cycloartanes from the leaves of Aglaia elliptica.

Authors:  A Inada; T Sorano; H Murata; Y Inatomi; D Darnaedi; T Nakanishi
Journal:  Chem Pharm Bull (Tokyo)       Date:  2001-09       Impact factor: 1.645

8.  A biomimetic approach to the rocaglamides employing photogeneration of oxidopyryliums derived from 3-hydroxyflavones.

Authors:  Baudouin Gerard; Guilford Jones Ii; John A Porco
Journal:  J Am Chem Soc       Date:  2004-10-27       Impact factor: 15.419

9.  Silvestrol and episilvestrol, potential anticancer rocaglate derivatives from Aglaia silvestris.

Authors:  Bang Yeon Hwang; Bao-Ning Su; Heebyung Chai; Qiuwen Mi; Leonardus B S Kardono; Johar J Afriastini; Soedarsono Riswan; Bernard D Santarsiero; Andrew D Mesecar; Robert Wild; Craig R Fairchild; Gregory D Vite; William C Rose; Norman R Farnsworth; Geoffrey A Cordell; John M Pezzuto; Steven M Swanson; A Douglas Kinghorn
Journal:  J Org Chem       Date:  2004-05-14       Impact factor: 4.354

10.  PAF antagonism in vitro and in vivo by aglafoline from Aglaia elliptifolia Merr.

Authors:  F N Ko; T S Wu; M J Liou; T F Huang; C M Teng
Journal:  Eur J Pharmacol       Date:  1992-07-21       Impact factor: 4.432
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  13 in total

1.  Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones.

Authors:  Olga A Mukhina; Andrei G Kutateladze
Journal:  J Am Chem Soc       Date:  2016-02-16       Impact factor: 15.419

Review 2.  Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species.

Authors:  Li Pan; John L Woodard; David M Lucas; James R Fuchs; A Douglas Kinghorn
Journal:  Nat Prod Rep       Date:  2014-05-02       Impact factor: 13.423

3.  Total Syntheses of the Isomeric Aglain Natural Products Foveoglin A and Perviridisin B: Selective Excited-State Intramolecular Proton-Transfer Photocycloaddition.

Authors:  Wenyu Wang; Anthony Clay; Retheesh Krishnan; Neil J Lajkiewicz; Lauren E Brown; Jayaraman Sivaguru; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-13       Impact factor: 15.336

4.  Inhibiting the oncogenic translation program is an effective therapeutic strategy in multiple myeloma.

Authors:  Salomon Manier; Daisy Huynh; Yu J Shen; Jia Zhou; Timur Yusufzai; Karma Z Salem; Richard Y Ebright; Jiantao Shi; Jihye Park; Siobhan V Glavey; William G Devine; Chia-Jen Liu; Xavier Leleu; Bruno Quesnel; Catherine Roche-Lestienne; John K Snyder; Lauren E Brown; Nathanael Gray; James Bradner; Luke Whitesell; John A Porco; Irene M Ghobrial
Journal:  Sci Transl Med       Date:  2017-05-10       Impact factor: 17.956

5.  Intercepted Retro-Nazarov Reaction: Syntheses of Amidino-Rocaglate Derivatives and Their Biological Evaluation as eIF4A Inhibitors.

Authors:  Wenhan Zhang; Jennifer Chu; Andrew M Cyr; Han Yueh; Lauren E Brown; Tony T Wang; Jerry Pelletier; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-30       Impact factor: 15.419

6.  Oxidopyrylium [5+2] Cycloaddition Chemistry: Historical Perspective and Recent Advances (2008-2018).

Authors:  Lauren P Bejcek; Ryan P Murelli
Journal:  Tetrahedron       Date:  2018-04-05       Impact factor: 2.457

7.  Synthesis of Aza-Rocaglates via ESIPT-Mediated (3+2) Photocycloaddition.

Authors:  Wenyu Wang; Regina Cencic; Luke Whitesell; Jerry Pelletier; John A Porco
Journal:  Chemistry       Date:  2016-07-15       Impact factor: 5.236

8.  Chemical Synthesis Enables Structural Reengineering of Aglaroxin C Leading to Inhibition Bias for Hepatitis C Viral Infection.

Authors:  Wenhan Zhang; Shufeng Liu; Rayelle I Maiga; Jerry Pelletier; Lauren E Brown; Tony T Wang; John A Porco
Journal:  J Am Chem Soc       Date:  2019-01-11       Impact factor: 15.419

9.  Biomimetic kinetic resolution: highly enantio- and diastereoselective transfer hydrogenation of aglain ketones to access flavagline natural products.

Authors:  Steven D Stone; Neil J Lajkiewicz; Luke Whitesell; Ahmed Hilmy; John A Porco
Journal:  J Am Chem Soc       Date:  2014-12-29       Impact factor: 15.419

10.  Remodeling natural products: chemistry and serine hydrolase activity of a rocaglate-derived β-lactone.

Authors:  Neil J Lajkiewicz; Armand B Cognetta; Micah J Niphakis; Benjamin F Cravatt; John A Porco
Journal:  J Am Chem Soc       Date:  2014-02-04       Impact factor: 15.419
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