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Literature DB >> 20161178

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

Christopher J Morten¹, Timothy F Jamison.

Abstract

This report describes a number of new synthetic approaches towards methyl-substituted mono- and diepoxy alcohols that serve as substrates for endo-selective epoxide-opening cascades. The key transformations involve the manipulation of alkynes. Highlighted are the directed methylmetalation of bishomopropargylic alcohols, the bromoallylation of alkynes, and Pd-catalyzed cross-coupling between an alkenyl boronate ester and allylic bromides.

Entities: Chemical Disease Gene

Year: 2009 PMID： 20161178 PMCID： PMC2724682 DOI： 10.1016/j.tet.2009.05.074

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

31 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. Practical synthesis of Shi's diester fructose derivative for catalytic asymmetric epoxidation of alkenes.

Authors: N Nieto; P Molas; J Benet-Buchholz; A Vidal-Ferran
Journal: J Org Chem Date: 2005-11-25 Impact factor: 4.354

Review 3. Allylstannanes and vinylstannanes from stannylcupration of C-C multiple bonds. Recent advances and applications in organic synthesis.

Authors: Asunción Barbero; Francisco J Pulido
Journal: Chem Soc Rev Date: 2005-09-13 Impact factor: 54.564

4. Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

Authors: Yian Shi
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

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

Authors: Christopher J Morten; Timothy F Jamison
Journal: J Am Chem Soc Date: 2009-05-20 Impact factor: 15.419

6. Multifunctional palladium catalysis. 2. Tandem haloallylation followed by Wacker-Tsuji oxidation or sonogashira cross-coupling.

Authors: Avinash N Thadani; Viresh H Rawal
Journal: Org Lett Date: 2002-11-28 Impact factor: 6.005

7. SiMe3-based homologation-epoxidation-cyclization strategy for ladder THP synthesis.

Authors: Timothy P Heffron; Timothy F Jamison
Journal: Org Lett Date: 2003-06-26 Impact factor: 6.005

8. 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

9. 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

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

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

2. Practical synthesis of Shi's diester fructose derivative for catalytic asymmetric epoxidation of alkenes.

Review 3. Allylstannanes and vinylstannanes from stannylcupration of C-C multiple bonds. Recent advances and applications in organic synthesis.

4. Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

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

6. Multifunctional palladium catalysis. 2. Tandem haloallylation followed by Wacker-Tsuji oxidation or sonogashira cross-coupling.

7. SiMe3-based homologation-epoxidation-cyclization strategy for ladder THP synthesis.

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

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

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

1. Nickel-catalyzed allylic substitution of simple alkenes.

2. Nickel-catalyzed allylic substitution of simple alkenes.

3. Ladder polyether synthesis via epoxide-opening cascades directed by a disappearing trimethylsilyl group.

Review 4. Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades.

5. Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis.

6. A reductive coupling strategy towards ripostatin A.