Literature DB >> 26430283

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

Soma Maitra1, Jana L Markley1, Rambabu Chegondi1, Paul R Hanson1.   

Abstract

A phosphate tether-mediated ring-closing metathesis study towards the synthesis of P-stereogenic bicyclo[6.3.1]-, bicyclo[7.3.1]-, and bicyclo[8.3.1]phosphates is reported. This study demonstrates expanded utility of phosphate tether-mediated desymmetrization of C2-symmetric, 1,3-anti-diol dienes in generating complex medium to large, P-stereogenic bicyclo[n.3.1]phosphates..

Entities:  

Keywords:  P-stereogenic phosphate; bicyclic phosphate triester; desymmetrization; phosphate tether; ring-closing metathesis; tripodal coupling

Year:  2015        PMID： 26430283      PMCID： PMC4584409          DOI： 10.1016/j.tet.2015.06.016

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  22 in total

1.  Diastereoselective temporary silicon-tethered ring-closing-metathesis reactions with prochiral alcohols: a new approach to long-range asymmetric induction.

Authors:  P Andrew Evans; Jian Cui; Gerald P Buffone
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-17       Impact factor: 15.336

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

Review 3.  Temporary silicon-tethered ring-closing metathesis: recent advances in methodology development and natural product synthesis.

Authors:  Alen Čusak
Journal:  Chemistry       Date:  2012-04-11       Impact factor: 5.236

4.  Formal synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via desymmetrization by ring-closing metathesis.

Authors:  S D Burke; E A Voight
Journal:  Org Lett       Date:  2001-01-25       Impact factor: 6.005

5.  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

6.  Diastereoselective synthesis of P-stereogenic heterocycles via enyne ring-closing metathesis.

Authors:  James Stephen Harvey; Guy T Giuffredi; Véronique Gouverneur
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

7.  Diastereotopic differentiation on phosphorus templates via the ring-closing metathesis reaction.

Authors:  D S Stoianova; P R Hanson
Journal:  Org Lett       Date:  2000-06-15       Impact factor: 6.005

8.  Diastereoselective ring-closing metathesis: synthesis of P-stereogenic phosphinates from prochiral phosphinic acid derivatives.

Authors:  Katherine S Dunne; Fabrice Bisaro; Barbara Odell; Jean-Marc Paris; Véronique Gouverneur
Journal:  J Org Chem       Date:  2005-12-23       Impact factor: 4.354

9.  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

10.  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
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  1 in total

1.  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
  1 in total

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