Literature DB >> 16771486

Enantioselective photocycloaddition mediated by chiral Brønsted acids: asymmetric synthesis of the rocaglamides.

Baudouin Gerard1, Sheharbano Sangji, Daniel J O'Leary, John A Porco.   

Abstract

Enantioselective syntheses of methyl rocaglate and the related natural products rocaglamide and rocaglaol are outlined. The approach involves enantioselective [3 + 2] photocycloaddition promoted by chiral Brønsted acids (TADDOLs) to afford an aglain precursor followed by a ketol shift/reduction sequence to the rocaglate core.

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Year:  2006        PMID： 16771486     DOI： 10.1021/ja062621j

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


  36 in total

1.  Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: synthetic and biological studies.

Authors:  Christina M Rodrigo; Regina Cencic; Stéphane P Roche; Jerry Pelletier; John A Porco
Journal:  J Med Chem       Date:  2011-12-19       Impact factor: 7.446

2.  Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.

Authors:  Claire M Filloux; Stephen P Lathrop; Tomislav Rovis
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-16       Impact factor: 11.205

3.  Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

Authors:  John A Malona; Kevin Cariou; William T Spencer; Alison J Frontier
Journal:  J Org Chem       Date:  2012-01-26       Impact factor: 4.354

Review 4.  Chemical probes and drug leads from advances in synthetic planning and methodology.

Authors:  Christopher J Gerry; Stuart L Schreiber
Journal:  Nat Rev Drug Discov       Date:  2018-04-13       Impact factor: 84.694

Review 5.  Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae).

Authors:  Sherif S Ebada; Neil Lajkiewicz; John A Porco; Min Li-Weber; Peter Proksch
Journal:  Prog Chem Org Nat Prod       Date:  2011

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

Authors:  Neil J Lajkiewicz; Stéphane P Roche; Baudouin Gerard; John A Porco
Journal:  J Am Chem Soc       Date:  2012-07-25       Impact factor: 15.419

7.  A photochemical flow reactor for large scale syntheses of aglain and rocaglate natural product analogues.

Authors:  Han Yueh; Qiwen Gao; John A Porco; Aaron B Beeler
Journal:  Bioorg Med Chem       Date:  2017-06-11       Impact factor: 3.641

8.  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

9.  Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide.

Authors:  John A Malona; Kevin Cariou; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

10.  Flavaglines target primitive leukemia cells and enhance anti-leukemia drug activity.

Authors:  K P Callahan; M Minhajuddin; C Corbett; E D Lagadinou; R M Rossi; V Grose; M M Balys; L Pan; S Jacob; A Frontier; M R Grever; D M Lucas; A D Kinghorn; J L Liesveld; M W Becker; C T Jordan
Journal:  Leukemia       Date:  2014-02-28       Impact factor: 11.528
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