Literature DB >> 12418890

Skeletal diversity via a branched pathway: efficient synthesis of 29 400 discrete, polycyclic compounds and their arraying into stock solutions.

Ohyun Kwon1, Seung Bum Park, Stuart L Schreiber.   

Abstract

We report the synthesis and arraying of 29 400 structurally diverse and complex polycyclic carbocycles using diversity-oriented synthesis (DOS) and the "one bead-one stock solution" technology platform. Skeletal diversity, a difficult challenge in DOS, was achieved with a branching reaction pathway using one or two Diels-Alder reactions. This pathway yields small molecules having 10 different skeletons.

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Year:  2002        PMID: 12418890     DOI: 10.1021/ja028086e

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


  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.  Re-engineering natural products to engage new biological targets.

Authors:  Stephen E Motika; Paul J Hergenrother
Journal:  Nat Prod Rep       Date:  2020-11-18       Impact factor: 13.423

3.  Skeletal and Appendage Diversity as Design Elements in the Synthesis of a Discovery Library of Nonaromatic Polycyclic 5-Iminooxazolidin-2-ones, Hydantoins, and Acylureas.

Authors:  S Werner; D M Turner; P G Chambers; K M Brummond
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

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

Authors:  Shiying Shang; Hayato Iwadare; Daniel E Macks; Lisa M Ambrosini; Derek S Tan
Journal:  Org Lett       Date:  2007-04-17       Impact factor: 6.005

5.  A Diels-Alder Route to Angularly Functionalized Bicyclic Structures.

Authors:  Woo Han Kim; Jun Hee Lee; Baptiste Aussedat; Samuel J Danishefsky
Journal:  Tetrahedron       Date:  2010-08-01       Impact factor: 2.457

6.  Allene-alkyne cross-coupling for stereoselective synthesis of substituted 1,4-dienes and cross-conjugated trienes.

Authors:  Heidi L Shimp; Alissa Hare; Martin McLaughlin; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2008-04-14       Impact factor: 2.457

7.  3-Bromopenta-2,4-dienylsilane: a useful reagent for the preparation of [3]dendralenes and polycyclic compounds.

Authors:  Mohammed Rahif; Maryline Roux; Jérôme Thibonnet; Jean-Luc Parrain
Journal:  Mol Divers       Date:  2013-01-12       Impact factor: 2.943

8.  Emulating the logic of monoterpenoid alkaloid biogenesis to access a skeletally diverse chemical library.

Authors:  Song Liu; John S Scotti; Sergey A Kozmin
Journal:  J Org Chem       Date:  2013-08-27       Impact factor: 4.354

9.  Synthesis of cross-conjugated trienes by rhodium-catalyzed dimerization of monosubstituted allenes.

Authors:  Tomoya Miura; Tsuneaki Biyajima; Takeharu Toyoshima; Masahiro Murakami
Journal:  Beilstein J Org Chem       Date:  2011-05-09       Impact factor: 2.883

Review 10.  Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries.

Authors:  Christopher Cordier; Daniel Morton; Sarah Murrison; Adam Nelson; Catherine O'Leary-Steele
Journal:  Nat Prod Rep       Date:  2008-04-14       Impact factor: 13.423

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