Literature DB >> 18785743

De novo asymmetric synthesis and biological evaluation of the trisaccharide portion of PI-080 and vineomycin B2.

Xiaomei Yu1, George A O'Doherty.   

Abstract

A highly enantio- and diastereoselective synthesis of an alpha-L-aculose, alpha-L-rhodinose, and beta-D-olivose trisaccharide is described. The key transformations include the palladium-catalyzed glycosylation, Myers' reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. Significant apoptotic antitumor activity was found for this trisaccharide, which has implication for vineomycin B2 and PI-080 structure-activity relationship.

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Year:  2008        PMID： 18785743     DOI： 10.1021/ol801817f

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


  11 in total

1.  Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  RSC Adv       Date:  2016-11-24       Impact factor: 3.361

2.  Stereochemical survey of digitoxin monosaccharides: new anticancer analogues with enhanced apoptotic activity and growth inhibitory effect on human non-small cell lung cancer cell.

Authors:  Hua-Yu Leo Wang; Wenjun Xin; Maoquan Zhou; Todd A Stueckle; Yon Rojanasakul; George A O'Doherty
Journal:  ACS Med Chem Lett       Date:  2011-01-13       Impact factor: 4.345

3.  De novo asymmetric synthesis of fridamycin E.

Authors:  Qian Chen; Michael Mulzer; Pei Shi; Penny J Beuning; Geoffrey W Coates; George A O'Doherty
Journal:  Org Lett       Date:  2011-11-22       Impact factor: 6.005

4.  De novo asymmetric synthesis of oligo-rhamno di- and tri-saccharides related to the anthrax tetrasaccharide.

Authors:  Hua-Yu Leo Wang; Haibing Guo; George A O'Doherty
Journal:  Tetrahedron       Date:  2013-04-22       Impact factor: 2.457

5.  DE NOVO ASYMMETRIC APPROACH TO THE DISACCHARIDE PORTION OF SCH-47554.

Authors:  Xiaomei Yu; Miaosheng Li; George A O'Doherty
Journal:  Heterocycles       Date:  2010-09-15       Impact factor: 0.831

6.  Synthesis and direct comparison of the anticancer activities of phomopsolides D and E and two 7-oxa-/7-aza-analogues.

Authors:  Alhanouf Z Aljahdali; Seth A Freedman; Jana Scott; Miaosheng Li; George A O'Doherty
Journal:  Medchemcomm       Date:  2019-05-08       Impact factor: 3.597

7.  A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides: Oligosaccharide Chain Length-Dependent Induction of Caspase-9-Mediated Apoptosis.

Authors:  Anand Krishnan V Iyer; Maoquan Zhou; Neelam Azad; Hosam Elbaz; Leo Wang; Derek K Rogalsky; Yon Rojanasakul; George A O'Doherty; Joseph M Langenhan
Journal:  ACS Med Chem Lett       Date:  2010-07-12       Impact factor: 4.345

8.  Convergent de novo synthesis of vineomycinone B2 methyl ester.

Authors:  Qian Chen; Yashan Zhong; George A O'Doherty
Journal:  Chem Commun (Camb)       Date:  2013-08-04       Impact factor: 6.222

9.  One-pot catalytic asymmetric synthesis of pyranones.

Authors:  Kevin Cheng; Ann Rowley Kelly; Rachel A Kohn; Jessica F Dweck; Patrick J Walsh
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

Review 10.  Synthesis and biological study of the phomopsolide and phomopsolidone natural products.

Authors:  Alhanouf Z Aljahdali; Kathryn A Foster; George A O'Doherty
Journal:  Chem Commun (Camb)       Date:  2020-10-07       Impact factor: 6.222
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