Literature DB >> 21557625

Control of olefin geometry in macrocyclic ring-closing metathesis using a removable silyl group.

Yikai Wang1, Miguel Jimenez, Anders S Hansen, Eun-Ang Raiber, Stuart L Schreiber, Damian W Young.   

Abstract

Introducing a silyl group at one of the internal olefin positions in diolefinic substrates results in E-selective olefin formation in macrocyclic ring-forming metathesis. The application of this method to a range of macrocyclic (E)-alkenylsiloxanes is described. Protodesilylation of alkenylsiloxane products yields novel Z-configured macrocycles.

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Year:  2011        PMID: 21557625      PMCID: PMC5436309          DOI: 10.1021/ja202012s

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


  39 in total

1.  Asymmetric total synthesis of the 1-epi-aglycon of the cripowellins A and B.

Authors:  Dieter Enders; Achim Lenzen; Michael Backes; Carsten Janeck; Kelly Catlin; Marie-Isabelle Lannou; Jan Runsink; Gerhard Raabe
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

2.  Double C--H activation of an N-heterocyclic carbene ligand in a ruthenium olefin metathesis catalyst.

Authors:  Soon Hyeok Hong; Anatoly Chlenov; Michael W Day; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Stereoselectivity of macrocyclic ring-closing olefin metathesis.

Authors:  C W Lee; R H Grubbs
Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

Review 4.  Alkyne metathesis.

Authors:  Alois Furstner; Paul W Davies
Journal:  Chem Commun (Camb)       Date:  2005-02-28       Impact factor: 6.222

5.  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

6.  Development of a general, sequential, ring-closing metathesis/intramolecular cross-coupling reaction for the synthesis of polyunsaturated macrolactones.

Authors:  Scott E Denmark; Joseck M Muhuhi
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

7.  Potent, orally bioavailable calcitonin gene-related peptide receptor antagonists for the treatment of migraine: discovery of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1- (2,2,2-trifluoroethyl)azepan-3-yl]-4- (2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin- 1-yl)piperidine-1-carboxamide (MK-0974).

Authors:  Daniel V Paone; Anthony W Shaw; Diem N Nguyen; Christopher S Burgey; James Z Deng; Stefanie A Kane; Kenneth S Koblan; Christopher A Salvatore; Scott D Mosser; Victor K Johnston; Bradley K Wong; Cynthia M Miller-Stein; James C Hershey; Samuel L Graham; Joseph P Vacca; Theresa M Williams
Journal:  J Med Chem       Date:  2007-10-11       Impact factor: 7.446

8.  "Diversity oriented synthesis" of functionalized chiral tetrahydropyridines: potential GABA receptor agonists and azasugars from natural amino acids via a sequential Baylis-Hillman reaction and RCM protocol.

Authors:  Palakodety Radha Krishna; P Srinivas Reddy
Journal:  J Comb Chem       Date:  2008-04-15

9.  Catalytic Z-selective olefin cross-metathesis for natural product synthesis.

Authors:  Simon J Meek; Robert V O'Brien; Josep Llaveria; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2011-03-24       Impact factor: 49.962

10.  Syntheses of aminoalcohol-derived macrocycles leading to a small-molecule binder to and inhibitor of Sonic Hedgehog.

Authors:  Lee F Peng; Benjamin Z Stanton; Nicole Maloof; Xiang Wang; Stuart L Schreiber
Journal:  Bioorg Med Chem Lett       Date:  2009-09-25       Impact factor: 2.823

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  11 in total

1.  Effects of alkali metal ion cationization on fragmentation pathways of triazole-epothilone.

Authors:  Xiyan Duan; Guoan Luo; Yue Chen; Xianglei Kong
Journal:  J Am Soc Mass Spectrom       Date:  2012-03-31       Impact factor: 3.109

2.  Improved ruthenium catalysts for Z-selective olefin metathesis.

Authors:  Benjamin K Keitz; Koji Endo; Paresma R Patel; Myles B Herbert; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2011-12-09       Impact factor: 15.419

3.  A Highly Efficient Synthesis of Z-Macrocycles Using Stereoretentive, Ruthenium-Based Metathesis Catalysts.

Authors:  Tonia S Ahmed; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

4.  E- and Z-trisubstituted macrocyclic alkenes for natural product synthesis and skeletal editing.

Authors:  Yucheng Mu; Felix W W Hartrampf; Elsie C Yu; Katherine E Lounsbury; Richard R Schrock; Filippo Romiti; Amir H Hoveyda
Journal:  Nat Chem       Date:  2022-05-16       Impact factor: 24.274

5.  Stereoselective access to Z and E macrocycles by ruthenium-catalyzed Z-selective ring-closing metathesis and ethenolysis.

Authors:  Vanessa M Marx; Myles B Herbert; Benjamin K Keitz; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2012-12-21       Impact factor: 15.419

6.  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

7.  Molybdenum-based complexes with two aryloxides and a pentafluoroimido ligand: catalysts for efficient Z-selective synthesis of a macrocyclic trisubstituted alkene by ring-closing metathesis.

Authors:  Chenbo Wang; Fredrik Haeffner; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-10       Impact factor: 15.336

8.  Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis.

Authors:  Miao Yu; Chenbo Wang; Andrew F Kyle; Pavol Jakubec; Darren J Dixon; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2011-11-02       Impact factor: 49.962

Review 9.  Macrocyclic drugs and synthetic methodologies toward macrocycles.

Authors:  Xufen Yu; Dianqing Sun
Journal:  Molecules       Date:  2013-05-24       Impact factor: 4.411

10.  Stereoselective synthesis of macrocyclic peptides via a dual olefin metathesis and ethenolysis approach.

Authors:  Shane L Mangold; Robert H Grubbs
Journal:  Chem Sci       Date:  2015-05-21       Impact factor: 9.825

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