Literature DB >> 21341742

Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold.

Baudouin Gerard1, Jean-Charles Marié, Bhaumik A Pandya, Maurice D Lee, Haibo Liu, Lisa A Marcaurelle.   

Abstract

All stereoisomers of a highly functionalized 2,3-unsaturated C-glycoside can be accessed in 10-100 g quantities from readily available starting materials and reagents in 3-7 steps. These chiral scaffolds contain three stereogenic centers along with orthogonally protected functional groups for downstream reactivity.

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Year:  2011        PMID： 21341742      PMCID： PMC3073442          DOI： 10.1021/jo1022926

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


  23 in total

1.  Pathway development and pilot library realization in diversity-oriented synthesis: exploring Ferrier and Pauson-Khand reactions on a glycal template.

Authors:  Hideki Kubota; Jongwon Lim; Kristopher M Depew; Stuart L Schreiber
Journal:  Chem Biol       Date:  2002-02

Review 2.  Combinatorial carbohydrate chemistry.

Authors:  Lisa A Marcaurelle; Peter H Seeberger
Journal:  Curr Opin Chem Biol       Date:  2002-06       Impact factor: 8.822

3.  Diversity oriented synthesis of tricyclic compounds from glycals using the Ferrier and the Pauson-Khand reactions.

Authors:  Srinivas Hotha; Ashish Tripathi
Journal:  J Comb Chem       Date:  2005 Nov-Dec

4.  An approach to skeletal diversity using functional group pairing of multifunctional scaffolds.

Authors:  Eamon Comer; Erin Rohan; Li Deng; John A Porco
Journal:  Org Lett       Date:  2007-05-02       Impact factor: 6.005

5.  Modulation of receptor and receptor subtype affinities using diastereomeric and enantiomeric monosaccharide scaffolds as a means to structural and biological diversity. A new route to ether synthesis.

Authors:  R Hirschmann; J Hynes; M A Cichy-Knight; R D van Rijn; P A Sprengeler; P G Spoors; W C Shakespeare; S Pietranico-Cole; J Barbosa; J Liu; W Yao; S Rohrer; A B Smith
Journal:  J Med Chem       Date:  1998-04-23       Impact factor: 7.446

6.  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

7.  An aldol-based build/couple/pair strategy for the synthesis of medium- and large-sized rings: discovery of macrocyclic histone deacetylase inhibitors.

Authors:  Lisa A Marcaurelle; Eamon Comer; Sivaraman Dandapani; Jeremy R Duvall; Baudouin Gerard; Sarathy Kesavan; Maurice D Lee; Haibo Liu; Jason T Lowe; Jean-Charles Marie; Carol A Mulrooney; Bhaumik A Pandya; Ann Rowley; Troy D Ryba; Byung-Chul Suh; Jingqiang Wei; Damian W Young; Lakshmi B Akella; Nathan T Ross; Yan-Ling Zhang; Daniel M Fass; Surya A Reis; Wen-Ning Zhao; Stephen J Haggarty; Michelle Palmer; Michael A Foley
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

8.  Evaluation of a vitamin-cloaking strategy for oligopeptide therapeutics: biotinylated HIV-1 protease inhibitors.

Authors:  I Islam; K Y Ng; K T Chong; T J McQuade; J O Hui; K F Wilkinson; B D Rush; M J Ruwart; R T Borchardt; J F Fisher
Journal:  J Med Chem       Date:  1994-01-21       Impact factor: 7.446

9.  Acceptor-substrate recognition by N-acetylglucosaminyltransferase-V: critical role of the 4"-hydroxyl group in beta-D-GlcpNAc-(1-->2)-alpha-D-Manp(1-->6)-beta-D-Glcp-OR.

Authors:  O Kanie; S C Crawley; M M Palcic; O Hindsgaul
Journal:  Carbohydr Res       Date:  1993-04-23       Impact factor: 2.104

10.  Selective mono-Claisen rearrangement of carbohydrate glycals. A chemical consequence of the vinylogous anomeric effect.

Authors:  D P Curran; Y G Suh
Journal:  Carbohydr Res       Date:  1987-12-31       Impact factor: 2.104
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  4 in total

1.  Fragment-based domain shuffling approach for the synthesis of pyran-based macrocycles.

Authors:  Eamon Comer; Haibo Liu; Adrien Joliton; Alexandre Clabaut; Christopher Johnson; Lakshmi B Akella; Lisa A Marcaurelle
Journal:  Proc Natl Acad Sci U S A       Date:  2011-03-07       Impact factor: 11.205

2.  Design, synthesis and in vitro splicing inhibition of desmethyl and carba-derivatives of herboxidiene.

Authors:  Arun K Ghosh; Kai Lv; Nianchun Ma; Emilio L Cárdenas; Kerstin A Effenberger; Melissa S Jurica
Journal:  Org Biomol Chem       Date:  2016-05-18       Impact factor: 3.876

3.  Synthesis of stereochemically and skeletally diverse fused ring systems from functionalized C-glycosides.

Authors:  Baudouin Gerard; Maurice D Lee; Sivaraman Dandapani; Jeremy R Duvall; Mark E Fitzgerald; Sarathy Kesavan; Jason T Lowe; Jean-Charles Marié; Bhaumik A Pandya; Byung-Chul Suh; Morgan Welzel O'Shea; Michael Dombrowski; Diane Hamann; Berenice Lemercier; Tiffanie Murillo; Lakshmi B Akella; Michael A Foley; Lisa A Marcaurelle
Journal:  J Org Chem       Date:  2013-05-21       Impact factor: 4.354

4.  Pre-mRNA splicing-modulatory pharmacophores: the total synthesis of herboxidiene, a pladienolide-herboxidiene hybrid analog and related derivatives.

Authors:  Chandraiah Lagisetti; Maria V Yermolina; Lalit Kumar Sharma; Gustavo Palacios; Brett J Prigaro; Thomas R Webb
Journal:  ACS Chem Biol       Date:  2013-12-30       Impact factor: 5.100
  4 in total

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