Literature DB >> 23264750

Divalent and Multivalent Activation in Phosphate Triesters: A Versatile Method for the Synthesis of Advanced Polyol Synthons.

Christopher D Thomas1, James P McParland, Paul R Hanson.   

Abstract

The construction of mono- and bicyclic phosphate trimesters possessing divalent and multivalent activation and their subsequent use in the production of advanced polyol synthons is presented. The method highlights efforts to employ phosphate tethers as removable, functionally active tethers capable of multipositional activation and their subsequent role as leaving groups in selective cleavage reactions. The development of phosphate tethers represents an integrated platform for a new and versatile tether for natural product synthesis and sheds light on new approaches to the facile construction of small molecules.

Entities:  

Year:  2009        PMID: 23264750      PMCID: PMC3526009          DOI: 10.1002/ejoc.200900560

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  33 in total

1.  Tandem catalysis: the sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes.

Authors:  J Louie; C W Bielawski; R H Grubbs
Journal:  J Am Chem Soc       Date:  2001-11-14       Impact factor: 15.419

2.  Desymmetrization by ring-closing metathesis leading to 6,8-dioxabicyclo[3.2.1]octanes: a new route for the synthesis of (+)-exo- and endo-brevicomin.

Authors:  S D Burke; N Müller; C M Beaudry
Journal:  Org Lett       Date:  1999-12-02       Impact factor: 6.005

3.  Temporary phosphate tethers: a metathesis strategy to differentiated polyol subunits.

Authors:  Joshua D Waetzig; Paul R Hanson
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

4.  Multivalent activation in temporary phosphate tethers: a new tether for small molecule synthesis.

Authors:  Alan Whitehead; Matthew D McReynolds; Joel D Moore; Paul R Hanson
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

5.  Total synthesis of (-)-salicylihalamide A.

Authors:  B B Snider; F Song
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

6.  Synthesis of the C1-C17 segment of phorboxazole B.

Authors:  Brian S Lucas; Laura M Luther; Steven D Burke
Journal:  Org Lett       Date:  2004-08-19       Impact factor: 6.005

7.  Diastereoselective palladium-catalyzed formate reduction of allylic carbonates en route to polypropionate systems.

Authors:  Anh Chau; Jean-François Paquin; Mark Lautens
Journal:  J Org Chem       Date:  2006-03-03       Impact factor: 4.354

8.  Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates.

Authors:  Umberto Piarulli; Christelle Claverie; Philippe Daubos; Cesare Gennari; Adriaan J Minnaard; Ben L Feringa
Journal:  Org Lett       Date:  2003-11-13       Impact factor: 6.005

9.  Highly anti-selective SN2' substitutions of chiral cyclic 2-iodo-allylic alcohol derivatives with mixed zinc-copper reagents.

Authors:  M Isabel Calaza; Eike Hupe; Paul Knochel
Journal:  Org Lett       Date:  2003-04-03       Impact factor: 6.005

10.  A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D.

Authors:  Alan Whitehead; Joshua D Waetzig; Christopher D Thomas; Paul R Hanson
Journal:  Org Lett       Date:  2008-03-07       Impact factor: 6.005

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  13 in total

1.  ROMP-derived oligomeric phosphates for application in facile benzylation.

Authors:  Toby R Long; Pradip K Maity; Thiwanka B Samarakoon; Paul R Hanson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

2.  Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of Medium to Large, P-Stereogenic Bicyclo[n.3.1]phosphates.

Authors:  Soma Maitra; Jana L Markley; Rambabu Chegondi; Paul R Hanson
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

3.  Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides.

Authors:  Kyle A DeKorver; Mary C Walton; Troy D North; Richard P Hsung
Journal:  Org Lett       Date:  2011-08-17       Impact factor: 6.005

4.  A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin.

Authors:  Phanindra K M Venukadasula; Rambabu Chegondi; Soma Maitra; Paul R Hanson
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

5.  Phosphate tether-mediated approach to the formal total synthesis of (-)-salicylihalamides A and B.

Authors:  Rambabu Chegondi; Mary M L Tan; Paul R Hanson
Journal:  J Org Chem       Date:  2011-04-19       Impact factor: 4.354

6.  Synthetic Studies to Lyngbouilloside: A Phosphate Tether-Mediated Synthesis of the Macrolactone Core.

Authors:  Rambabu Chegondi; Paul R Hanson
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

7.  Phosphate-tether-mediated ring-closing metathesis for the preparation of complex 1,3-anti-diol-containing subunits.

Authors:  Rambabu Chegondi; Soma Maitra; Jana L Markley; Paul R Hanson
Journal:  Chemistry       Date:  2013-05-24       Impact factor: 5.236

8.  An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.

Authors:  Susanthi Jayasinghe; Phanindra K M Venukadasula; Paul R Hanson
Journal:  Org Lett       Date:  2013-12-02       Impact factor: 6.005

9.  Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of P-Stereogenic, Z-Configured Bicyclo[7.3.1]- and Bicyclo[8.3.1]phosphates.

Authors:  Jana L Markley; Soma Maitra; Paul R Hanson
Journal:  J Org Chem       Date:  2016-01-21       Impact factor: 4.354

10.  A phosphate tether-mediated, one-pot, sequential ring-closing metathesis/cross-metathesis/chemoselective hydrogenation protocol.

Authors:  Phanindra K M Venukadasula; Rambabu Chegondi; Gregory M Suryn; Paul R Hanson
Journal:  Org Lett       Date:  2012-05-08       Impact factor: 6.005

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