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Literature DB >> 19402635

Water overcomes methyl group directing effects in epoxide-opening cascades.

Christopher J Morten¹, Timothy F Jamison.

Abstract

Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, water can overcome the powerful electronic directing effect of a methyl substituent at either site of the epoxide, making water a uniquely versatile medium and promoter of epoxide opening.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2009 PMID： 19402635 PMCID： PMC2803343 DOI： 10.1021/ja9025243

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

8 in total

1. Reagent-controlled switching of 5-exo to 6-endo cyclizations in epoxide openings.

Authors: Yoshiki Morimoto; Yoshihiro Nishikawa; Chigusa Ueba; Takeshi Tanaka
Journal: Angew Chem Int Ed Engl Date: 2006-01-23 Impact factor: 15.336

2. Biomimetic synthesis of trans,syn,trans-fused polyoxepanes: remarkable substituent effects on the endo-regioselective oxacyclization of polyepoxides.

Authors: Jason C Valentine; Frank E McDonald; Wade A Neiwert; Kenneth I Hardcastle
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

3. Epoxide-opening cascades promoted by water.

Authors: Ivan Vilotijevic; Timothy F Jamison
Journal: Science Date: 2007-08-31 Impact factor: 47.728

Review 4. The chemistry of brevetoxins: a review.

Authors: K Nakanishi
Journal: Toxicon Date: 1985 Impact factor: 3.033

5. Biomimetic synthesis of fused polypyrans: oxacyclization stereo- and regioselectivity is a function of the nucleophile.

Authors: Fernando Bravo; Frank E McDonald; Wade A Neiwert; Bao Do; Kenneth I Hardcastle
Journal: Org Lett Date: 2003-06-12 Impact factor: 6.005

6. Analysis of specific mutants in the lasalocid gene cluster: evidence for enzymatic catalysis of a disfavoured polyether ring closure.

Authors: Luke Smith; Hui Hong; Jonathan B Spencer; Peter F Leadlay
Journal: Chembiochem Date: 2008-12-15 Impact factor: 3.164

7. An experimental and computational approach to defining structure/reactivity relationships for intramolecular addition reactions to bicyclic epoxonium ions.

Authors: Shuangyi Wan; Hakan Gunaydin; K N Houk; Paul E Floreancig
Journal: J Am Chem Soc Date: 2007-06-05 Impact factor: 15.419

8. Alkene substituents for selective activation of endo-regioselective polyepoxide oxacyclizations.

Authors: Fernando Bravo; Frank E McDonald; Wade A Neiwert; Kenneth I Hardcastle
Journal: Org Lett Date: 2004-11-25 Impact factor: 6.005

8 in total

22 in total

1. Lessons and revelations from biomimetic syntheses.

Authors: Mina Razzak; Jef K De Brabander
Journal: Nat Chem Biol Date: 2011-11-15 Impact factor: 15.040

2. New synthetic strategies for the stereocontrolled synthesis of substituted "skipped" diepoxides.

Authors: Christopher J Morten; Timothy F Jamison
Journal: Tetrahedron Date: 2009-08-15 Impact factor: 2.457

3. Entropic factors provide unusual reactivity and selectivity in epoxide-opening reactions promoted by water.

Authors: Jeffery A Byers; Timothy F Jamison
Journal: Proc Natl Acad Sci U S A Date: 2013-09-17 Impact factor: 11.205

4. Hydroxyl-substituted ladder polyethers via selective tandem epoxidation/cyclization sequence.

Authors: Lara C Czabaniuk; Timothy F Jamison
Journal: Org Lett Date: 2015-02-03 Impact factor: 6.005

Review 5. The development of endo-selective epoxide-opening cascades in water.

Authors: Christopher J Morten; Jeffery A Byers; Aaron R Van Dyke; Ivan Vilotijevic; Timothy F Jamison
Journal: Chem Soc Rev Date: 2009-09-16 Impact factor: 54.564

6. Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes.

Authors: Catherine P McGeough; Alexandra E Strom; Timothy F Jamison
Journal: Org Lett Date: 2019-05-02 Impact factor: 6.005

7. Absolute configuration of brevisamide and brevisin: confirmation of a universal biosynthetic process for Karenia brevis polyethers.

Authors: Ryan M Van Wagoner; Masayuki Satake; Andrea J Bourdelais; Daniel G Baden; Jeffrey L C Wright
Journal: J Nat Prod Date: 2010-06-25 Impact factor: 4.050

8. Zirconium(IV)- and hafnium(IV)-catalyzed highly enantioselective epoxidation of homoallylic and bishomoallylic alcohols.

Authors: Zhi Li; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2010-06-16 Impact factor: 15.419

Review 9. Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades.

Authors: Ivan Vilotijevic; Timothy F Jamison
Journal: Mar Drugs Date: 2010-03-19 Impact factor: 5.118

10. A dioxane template for highly selective epoxy alcohol cyclizations.

Authors: James J Mousseau; Christopher J Morten; Timothy F Jamison
Journal: Chemistry Date: 2013-06-17 Impact factor: 5.236