Literature DB >> 16186897

Polyketide stereotetrads in natural products.

Ari M P Koskinen1, Kaisa Karisalmi.   

Abstract

Natural products (or secondary metabolites) remain as the most important source for discovery of new and potential drug molecules. With high resolution data of their structures, and the advancement of synthesis possibilities, analysis of the natural products based on their specific structural features is valuable to those entering the field. In this tutorial review we attempt such an analysis indicating the salient features of the structural classes with examples of the synthesis of each one of them. As the particular class of natural products, we have chosen polyketides.

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Year:  2005        PMID: 16186897     DOI: 10.1039/b417466f

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  24 in total

1.  Rapid and stereochemically flexible synthesis of polypropionates: super-silyl-governed aldol cascades.

Authors:  Patrick B Brady; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-17       Impact factor: 15.336

2.  A highly enantio- and diastereoselective 1,3-dimethylallylation of aldehydes.

Authors:  Yu Yuan; Amy J Lai; Christina M Kraml; Chulbom Lee
Journal:  Tetrahedron       Date:  2006-12-04       Impact factor: 2.457

3.  The supersilyl group as a carboxylic acid protecting group: application to highly stereoselective aldol and Mannich reactions.

Authors:  Jiajing Tan; Matsujiro Akakura; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-29       Impact factor: 15.336

4.  Super silyl stereo-directing groups for complete 1,5-syn and -anti stereoselectivities in the aldol reactions of beta-siloxy methyl ketones with aldehydes.

Authors:  Yousuke Yamaoka; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

5.  Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

Authors:  Xin Gao; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

6.  Iterative assembly line synthesis of polypropionates with full stereocontrol.

Authors:  Teerawut Bootwicha; Julian M Feilner; Eddie L Myers; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2017-04-10       Impact factor: 24.427

7.  Total synthesis of (+)-roxaticin via C-C bond forming transfer hydrogenation: a departure from stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles in polyketide construction.

Authors:  Soo Bong Han; Abbas Hassan; In Su Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

8.  Stereoselective construction of all-anti polypropionate modules: synthesis of the C5-C10 fragment of streptovaricin U.

Authors:  Wildeliz Torres; Raúl R Rodríguez; José A Prieto
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

9.  β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

Authors:  Jakub Saadi; Hisashi Yamamoto
Journal:  Chemistry       Date:  2013-02-19       Impact factor: 5.236

10.  Total synthesis of (+)-trienomycins A and F via C-C bond-forming hydrogenation and transfer hydrogenation.

Authors:  David J Del Valle; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-07-17       Impact factor: 15.419

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