Literature DB >> 21780843

Total synthesis of landomycin A, a potent antitumor angucycline antibiotic.

Xiaoyu Yang1, Boqiao Fu, Biao Yu.   

Abstract

The first total synthesis of landomycin A, the longest and most potent antitumor angucycline antibiotic, has been achieved in 63 steps and 0.34% overall yield starting from 2,5-dihydroxybenzoic acid, 3,5-dimethylphenol, triacetyl d-glucal, and d-xylose, with a convergent linear sequence of 21 steps.

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Year:  2011        PMID： 21780843     DOI： 10.1021/ja205339p

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


  13 in total

Review 1.  Methods for 2-Deoxyglycoside Synthesis.

Authors:  Clay S Bennett; M Carmen Galan
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

2.  Ruthenium(0) Catalyzed Endiyne-α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C-C Bond Forming Transfer Hydrogenation.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

3.  Recent Advances in Transition Metal-Catalyzed Glycosylation.

Authors:  Matthew J McKay; Hien M Nguyen
Journal:  ACS Catal       Date:  2012-06-14       Impact factor: 13.084

4.  Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach.

Authors:  Subbarao Yalamanchili; Dina Lloyd; Clay S Bennett
Journal:  Org Lett       Date:  2019-04-25       Impact factor: 6.005

Review 5.  Delineation of gilvocarcin, jadomycin, and landomycin pathways through combinatorial biosynthetic enzymology.

Authors:  Madan K Kharel; Jürgen Rohr
Journal:  Curr Opin Chem Biol       Date:  2012-03-30       Impact factor: 8.822

6.  Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide.

Authors:  Joseph R Romeo; Luca McDermott; Clay S Bennett
Journal:  Org Lett       Date:  2020-04-13       Impact factor: 6.005

7.  Ruthenium(0)-Catalyzed [4+2] Cycloaddition of Acetylenic Aldehydes with α-Ketols: Convergent Construction of Angucycline Ring Systems.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-09       Impact factor: 15.336

8.  Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.

Authors:  Brett R Ambler; Ben W H Turnbull; Sankar Rao Suravarapu; Maulen M Uteuliyev; Nancy O Huynh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-11       Impact factor: 15.419

9.  Grincamycins P-T: Rearranged Angucyclines from the Marine Sediment-Derived Streptomyces sp. CNZ-748 Inhibit Cell Lines of the Rare Cancer Pseudomyxoma Peritonei.

Authors:  Zhuo Shang; Zachary E Ferris; Douglas Sweeney; Alexander B Chase; Chunhua Yuan; Yvonne Hui; Lukuan Hou; Ethan A Older; Dan Xue; Xiaoyu Tang; Weipeng Zhang; Prakash Nagarkatti; Mitzi Nagarkatti; Traci L Testerman; Paul R Jensen; Jie Li
Journal:  J Nat Prod       Date:  2021-04-26       Impact factor: 4.050

10.  Excited-State Palladium-Catalyzed 1,2-Spin-Center Shift Enables Selective C-2 Reduction, Deuteration, and Iodination of Carbohydrates.

Authors:  Gaoyuan Zhao; Wang Yao; Jaclyn N Mauro; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2021-01-19       Impact factor: 15.419
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