Literature DB >> 16119915

Stereospecific synthesis of (+/-)-1,2-anhydro methyl rocaglate.

Philip Magnus1, Matthew A H Stent.   

Abstract

The rocaglates and analogues thereof have recently become targets for synthesis because of their potent antitumor activity. One of the major difficulties has been the control of stereochemistry of the adjacent -Ph and -An groups. In this letter we show that 14 is converted into 5 as a single stereoisomer and subsequently transformed into 1,2-anhydro methyl rocaglate 20. [reaction: see text]

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Year:  2005        PMID: 16119915     DOI: 10.1021/ol0513793

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


  8 in total

1.  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 2.  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

3.  Synthesis of (±)-tetrapetalone A-Me aglycon.

Authors:  Peter N Carlsen; Tyler J Mann; Amir H Hoveyda; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-07       Impact factor: 15.336

4.  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

5.  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

6.  Synthesis of α-diketones from alkylaryl- and diarylalkynes using mercuric salts.

Authors:  Michael E Jung; Gang Deng
Journal:  Org Lett       Date:  2014-04-01       Impact factor: 6.005

7.  No acid required: 4π and 6π electrocyclization reactions of dienyl diketones for the synthesis of cyclopentenones and 2H-Pyrans.

Authors:  Steven D Jacob; Joshua L Brooks; Alison J Frontier
Journal:  J Org Chem       Date:  2014-10-17       Impact factor: 4.354

8.  Enantioselective synthesis of cyclopenta[b]benzofurans via an organocatalytic intramolecular double cyclization.

Authors:  Bruno Matos Paz; Yang Li; Mathias Kirk Thøgersen; Karl Anker Jørgensen
Journal:  Chem Sci       Date:  2017-10-02       Impact factor: 9.825

  8 in total

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