Literature DB >> 16018610

Concise syntheses of (+)-macrosphelides A and B.

Seung-Mann Paek1, Seung-Yong Seo, Seok-Ho Kim, Jong-Wha Jung, Yong-Sil Lee, Jae-Kyung Jung, Young-Ger Suh.   

Abstract

[reaction: see text]. Unified and highly convergent total syntheses of (+)-macrosphelides A and B are described. Key features of the syntheses include (1) concise synthesis of the optically active delta-hydroxy-gamma-keto alpha,beta-unsaturated acid fragment via the direct addition of a trans-vinylogous ester anion equivalent to the readily available Weinreb amide and (2) facile construction of the 16-membered macrolide core of the macrosphelide series via an intramolecular nitrile-oxide cycloaddition (INOC).

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Year:  2005        PMID: 16018610     DOI: 10.1021/ol0508429

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


  5 in total

1.  Binary fluorous tagging enables the synthesis and separation of a 16-stereoisomer library of macrosphelides.

Authors:  Dennis P Curran; Mantosh K Sinha; Kai Zhang; Jesse J Sabatini; Dae-Hyun Cho
Journal:  Nat Chem       Date:  2012-01-10       Impact factor: 24.427

2.  Structure Elucidation of Nigricanoside A Through Enantioselective Total Synthesis.

Authors:  Jie Chen; Panduka Koswatta; J Robb DeBergh; Peng Fu; Ende Pan; John B MacMillan; Joseph M Ready
Journal:  Chem Sci       Date:  2015-03-12       Impact factor: 9.825

3.  Development of an advanced synthetic route to macrosphelides and its application to the discovery of a more potent macrosphelide derivative.

Authors:  Yu Mi Heo; Hunseok Lee; Young Kee Shin; Seung-Mann Paek
Journal:  Molecules       Date:  2014-09-29       Impact factor: 4.411

4.  Synthetic studies on bioactive natural polyketides: intramolecular nitrile oxide-olefin cycloaddition approach for construction of a macrolactone skeleton of macrosphelide B.

Authors:  Seung-Mann Paek; Young-Ger Suh
Journal:  Molecules       Date:  2011-06-10       Impact factor: 4.411

Review 5.  Design and Synthesis of Anti-Cancer Chimera Molecules Based on Marine Natural Products.

Authors:  Min Woo Ha; Bo Reum Song; Hye Jin Chung; Seung-Mann Paek
Journal:  Mar Drugs       Date:  2019-08-27       Impact factor: 5.118

  5 in total

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