Literature DB >> 12536807

Versatile enantiocontrolled synthesis of (+)-fostriecin.

Tomoyuki Esumi1, Nanako Okamoto, Susumi Hatakeyama.   

Abstract

Fostriecin, a potent protein phosphatase inhibitor and antitumor agent, has been enantioselectively synthesized in naturally occurring form via a versatile route, which also allows one to secure all possible stereoisomeres of the C1-C13 fragment including the C11 stereocenter and the geometry of the delta 12-double bond.

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Year:  2002        PMID： 12536807     DOI： 10.1039/b209742g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  9 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.  Structure-activity relationship studies of fostriecin, cytostatin, and key analogs, with PP1, PP2A, PP5, and( beta12-beta13)-chimeras (PP1/PP2A and PP5/PP2A), provide further insight into the inhibitory actions of fostriecin family inhibitors.

Authors:  Mark R Swingle; Lauren Amable; Brian G Lawhorn; Suzanne B Buck; Christopher P Burke; Pukar Ratti; Kimberly L Fischer; Dale L Boger; Richard E Honkanen
Journal:  J Pharmacol Exp Ther       Date:  2009-07-10       Impact factor: 4.030

8.  Total synthesis and evaluation of phostriecin and key structural analogues.

Authors:  Christopher P Burke; Mark R Swingle; Richard E Honkanen; Dale L Boger
Journal:  J Org Chem       Date:  2010-07-29       Impact factor: 4.354

9.  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
  9 in total

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