Literature DB >> 11893198

Asymmetric total synthesis of (+)-fostriecin.

Y Krishna Reddy1, J R Falck.   

Abstract

[structure: see text] The title compound, a potent protein phosphatase inhibitor and anticancer agent, was prepared by an efficient, multiconvergent asymmetric synthesis. Key transformations include a ring forming olefin metathesis leading to the alpha,beta-unsaturated lactone and creation of the triene moiety via Suzuki cross-coupling.

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Year:  2002        PMID: 11893198     DOI: 10.1021/ol025537r

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


  15 in total

1.  Total synthesis and evaluation of cytostatin, its C10-C11 diastereomers, and additional key analogues: impact on PP2A inhibition.

Authors:  Brian G Lawhorn; Sobhana B Boga; Scott E Wolkenberg; David A Colby; Carla-Maria Gauss; Mark R Swingle; Lauren Amable; Richard E Honkanen; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

Review 2.  Synthetic Strategies Employed for the Construction of Fostriecin and Related Natural Products.

Authors:  Barry M Trost; Joshua D Knopf; Cheyenne S Brindle
Journal:  Chem Rev       Date:  2016-12-08       Impact factor: 60.622

3.  Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence.

Authors:  Dong Gao; George A O'Doherty
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

4.  Total and Formal Syntheses of Fostriecin.

Authors:  Gao Dong; Bohui Li; George O'Doherty
Journal:  Org Chem Front       Date:  2020-10-12       Impact factor: 5.281

Review 5.  De novo synthesis of natural products via the asymmetric hydration of polyenes.

Authors:  Yanping Wang; Yalan Xing; Qi Zhang; George A O'Doherty
Journal:  Chem Commun (Camb)       Date:  2011-05-11       Impact factor: 6.222

Review 6.  Genetic manipulation of the biosynthetic process leading to phoslactomycins, potent protein phosphatase 2A inhibitors.

Authors:  Mohini Ghatge; Nadaraj Palaniappan; Suparna Das Choudhuri; Kevin Reynolds
Journal:  J Ind Microbiol Biotechnol       Date:  2006-04-12       Impact factor: 3.346

7.  Synthesis of Z-(pinacolato)allylboron and Z-(pinacolato)alkenylboron compounds through stereoselective catalytic cross-metathesis.

Authors:  Elizabeth T Kiesewetter; Robert V O'Brien; Elsie C Yu; Simon J Meek; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2013-04-15       Impact factor: 15.419

8.  Phase I and pharmacokinetic study of fostriecin given as an intravenous bolus daily for five consecutive days.

Authors:  Lyly H Lê; Charles Erlichman; Linda Pillon; Jake J Thiessen; Andrew Day; Nancy Wainman; Elizabeth A Eisenhauer; Malcolm J Moore
Journal:  Invest New Drugs       Date:  2004-04       Impact factor: 3.850

9.  Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2-Propanol-Mediated Reductive Coupling.

Authors:  Gilmar A Brito; Franco Della-Felice; Guoshun Luo; Alexander S Burns; Ronaldo A Pilli; Scott D Rychnovsky; Michael J Krische
Journal:  Org Lett       Date:  2018-06-25       Impact factor: 6.005

10.  Total synthesis, assignment of the relative and absolute stereochemistry, and structural reassignment of phostriecin (aka Sultriecin).

Authors:  Christopher P Burke; Nadia Haq; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-02-24       Impact factor: 15.419

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