Literature DB >> 14535786

Lasonolide A: structural revision and total synthesis.

Ho Young Song1, Jung Min Joo, Jung Won Kang, Dae-Shik Kim, Cheol-Kyu Jung, Hyo Shin Kwak, Jin Hyun Park, Eun Lee, Chang Yong Hong, ShinWu Jeong, Kiwan Jeon, Ji Hyun Park.   

Abstract

The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of beta-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantiomers of a revised structure featuring 17E,25Z double bonds were synthesized, and the (-)-isomer was found to be the biologically active enantiomer.

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Year:  2003        PMID: 14535786     DOI: 10.1021/jo034930n

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  9 in total

1.  Stereoselective synthesis of both tetrahydropyran rings of the antitumor macrolide, (-)-lasonolide A.

Authors:  Arun K Ghosh; Guo-Bao Ren
Journal:  J Org Chem       Date:  2012-02-10       Impact factor: 4.354

2.  Total synthesis of (-)-pseudolaric acid B.

Authors:  Barry M Trost; Jerome Waser; Arndt Meyer
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

3.  Total Synthesis of (-)-Lasonolide A.

Authors:  Barry M Trost; Craig E Stivala; Daniel R Fandrick; Kami L Hull; Audris Huang; Caroline Poock; Rainer Kalkofen
Journal:  J Am Chem Soc       Date:  2016-09-01       Impact factor: 15.419

4.  The complexity of phosphorylated H2AX foci formation and DNA repair assembly at DNA double-strand breaks.

Authors:  Asako J Nakamura; V Ashutosh Rao; Yves Pommier; William M Bonner
Journal:  Cell Cycle       Date:  2010-01-29       Impact factor: 4.534

5.  Total synthesis of potent antitumor agent (-)-lasonolide A: a cycloaddition-based strategy.

Authors:  Arun K Ghosh; Gangli Gong
Journal:  Chem Asian J       Date:  2008-10-06

6.  Radicals in natural product synthesis.

Authors:  Kevin J Romero; Matthew S Galliher; Derek A Pratt; Corey R J Stephenson
Journal:  Chem Soc Rev       Date:  2018-10-29       Impact factor: 54.564

7.  Antibacterial Activity and Amphidinol Profiling of the Marine Dinoflagellate Amphidinium carterae (Subclade III).

Authors:  Maria Elena Barone; Elliot Murphy; Rachel Parkes; Gerard T A Fleming; Floriana Campanile; Olivier P Thomas; Nicolas Touzet
Journal:  Int J Mol Sci       Date:  2021-11-11       Impact factor: 5.923

Review 8.  Synthetic efforts on the road to marine natural products bearing 4-O-2,3,4,6-tetrasubstituted THPs: an update.

Authors:  Marta Fariña-Ramos; Celina García; Víctor S Martín; Sergio J Álvarez-Méndez
Journal:  RSC Adv       Date:  2021-02-03       Impact factor: 3.361

9.  Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes.

Authors:  M Emin Cinar; Bernward Engelen; Martin Panthöfer; Hans-Jörg Deiseroth; Jens Schlirf; Michael Schmittel
Journal:  Beilstein J Org Chem       Date:  2016-04-27       Impact factor: 2.883

  9 in total

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