Literature DB >> 17439132

A unified synthetic approach to polyketides having both skeletal and stereochemical diversity.

Shiying Shang1, Hayato Iwadare, Daniel E Macks, Lisa M Ambrosini, Derek S Tan.   

Abstract

An efficient systematic approach to the diversity-oriented synthesis of polyketides has been developed to provide both skeletal and stereochemical diversity. Each synthetic intermediate is also a desired polyketide fragment and no protecting group manipulations are required. A first-generation synthesis provides a 74-membered polyketide library comprising six different skeletal classes, each in one to five steps from propargylic alcohol precursors. A study of epoxyol opening reactions revealed unusual reactivity trends based on epoxide configuration.

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Year:  2007        PMID: 17439132      PMCID: PMC2597797          DOI: 10.1021/ol070405p

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


  31 in total

Review 1.  Target-oriented and diversity-oriented organic synthesis in drug discovery.

Authors:  S L Schreiber
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

2.  Pairwise use of complexity-generating reactions in diversity-oriented organic synthesis.

Authors:  D Lee; J K Sello; S L Schreiber
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

3.  A combinatorial scaffold approach toward kinase-directed heterocycle libraries.

Authors:  Sheng Ding; Nathanael S Gray; Xu Wu; Qiang Ding; Peter G Schultz
Journal:  J Am Chem Soc       Date:  2002-02-27       Impact factor: 15.419

4.  Synthetic strategy toward skeletal diversity via solid-supported, otherwise unstable reactive intermediates.

Authors:  Steven J Taylor; Alexander M Taylor; Stuart L Schreiber
Journal:  Angew Chem Int Ed Engl       Date:  2004-03-19       Impact factor: 15.336

5.  A synthesis strategy yielding skeletally diverse small molecules combinatorially.

Authors:  Martin D Burke; Eric M Berger; Stuart L Schreiber
Journal:  J Am Chem Soc       Date:  2004-11-03       Impact factor: 15.419

Review 6.  Assembly-line enzymology for polyketide and nonribosomal Peptide antibiotics: logic, machinery, and mechanisms.

Authors:  Michael A Fischbach; Christopher T Walsh
Journal:  Chem Rev       Date:  2006-08       Impact factor: 60.622

7.  High-affinity mu opioid receptor ligands discovered by the screening of an exhaustively stereodiversified library of 1,5-enediols.

Authors:  Bryce A Harrison; Tiffany Malinky Gierasch; Claire Neilan; Gavril W Pasternak; Gregory L Verdine
Journal:  J Am Chem Soc       Date:  2002-11-13       Impact factor: 15.419

8.  Exploring skeletal diversity via ring contraction of glycal-derived scaffolds.

Authors:  Adam R Yeager; Geanna K Min; John A Porco; Scott E Schaus
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

9.  High stereochemical diversity and applications for the synthesis of marine natural products: a library of carbohydrate mimics and polyketide segments

Authors: 
Journal:  Chemistry       Date:  2000-09-15       Impact factor: 5.236

10.  Building a small polypropionate library. Synthesis of all possible stereotetrads (building blocks for polyketide synthesis) from furan.

Authors:  O Arjona; R Menchaca; J Plumet
Journal:  J Org Chem       Date:  2001-04-06       Impact factor: 4.354

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  11 in total

1.  Diversity through a branched reaction pathway: generation of multicyclic scaffolds and identification of antimigratory agents.

Authors:  Zhiming Wang; Sabrina Castellano; Sape S Kinderman; Christian E Argueta; Anwar B Beshir; Gabriel Fenteany; Ohyun Kwon
Journal:  Chemistry       Date:  2010-11-09       Impact factor: 5.236

2.  Studies toward a library of tetrahydrofurans: click and MCR products of mono- and bis-tetrahydrofurans.

Authors:  Jitendra K Mishra; Peter Wipf; Subhash C Sinha
Journal:  J Comb Chem       Date:  2010-09-13

3.  Novel synthesis and biological evaluation of enigmols as therapeutic agents for treating prostate cancer.

Authors:  Ethel C Garnier-Amblard; Suzanne G Mays; Richard F Arrendale; Mark T Baillie; Anatoliy S Bushnev; Deborah G Culver; Taylor J Evers; Jason J Holt; Randy B Howard; Lanny S Liebeskind; David S Menaldino; Michael G Natchus; John A Petros; Harsha Ramaraju; G Prabhakar Reddy; Dennis C Liotta
Journal:  ACS Med Chem Lett       Date:  2011-03-25       Impact factor: 4.345

4.  Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer.

Authors:  Seung Wook Kim; Wonchul Lee; Michael J Krische
Journal:  Org Lett       Date:  2017-02-21       Impact factor: 6.005

5.  1,3-allylic strain as a strategic diversification element for constructing libraries of substituted 2-arylpiperidines.

Authors:  Thomas C Coombs; Gerald H Lushington; Justin Douglas; Jeffrey Aubé
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-23       Impact factor: 15.336

6.  Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a.

Authors:  Michael T Crimmins; Anne-Marie R Dechert
Journal:  Org Lett       Date:  2012-04-18       Impact factor: 6.005

7.  Unnatural polyketide analogues selectively target the HER signaling pathway in human breast cancer cells.

Authors:  Seok Joon Kwon; Moon Il Kim; Bosung Ku; Lydie Coulombel; Jin-Hwan Kim; Joseph H Shawky; Robert J Linhardt; Jonathan S Dordick
Journal:  Chembiochem       Date:  2010-03-01       Impact factor: 3.164

8.  Explorations of stemona alkaloid-inspired analogues: skeletal modification and functional group diversification.

Authors:  Kevin J Frankowski; Benjamin Neuenswander; Jeffrey Aubé
Journal:  J Comb Chem       Date:  2008-08-13

9.  Improved method for the synthesis of beta-carbonyl silyl-1,3-dithianes by the double conjugate addition of 1,3-dithiol to propargylic carbonyl compounds.

Authors:  Sumit Mukherjee; Dimitra Kontokosta; Aditi Patil; Sivakumar Rallapalli; Daesung Lee
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

10.  Parallel synthesis of an imidazole-4,5-dicarboxamide library bearing amino acid esters and alkanamines.

Authors:  Rosanna Solinas; John C DiCesare; Paul W Baures
Journal:  Molecules       Date:  2008-12-15       Impact factor: 4.411

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