Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Alkene substituents for selective activation of endo-regioselective polyepoxide oxacyclizations.

Literature DB >> 15548057

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

Fernando Bravo¹, Frank E McDonald, Wade A Neiwert, Kenneth I Hardcastle.

Abstract

The presence of an alkenyl substituent on the terminal epoxide of a polyepoxide substrate enhances the yield of all-endo-regioselective tandem oxacyclization to trans-syn-trans-fused polycyclic ethers. For a substrate in which the epoxide and alkene functional groups are separated by two methylene substituents, a novel bromonium ion-induced endo-regioselective cyclization to bromooxepane is also described. [reaction: see text]

Entities: Chemical Gene

Mesh：

Substances：

Year: 2004 PMID： 15548057 DOI： 10.1021/ol048212e

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

Keyword Cloud
Cited

16 in total

1. 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

Review 2. The continuing saga of the marine polyether biotoxins.

Authors: K C Nicolaou; Michael O Frederick; Robert J Aversa
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. 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

4. Total Synthesis of the Marine Ladder Polyether Gymnocin B.

Authors: Satapanawat Sittihan; Timothy F Jamison
Journal: J Am Chem Soc Date: 2019-07-08 Impact factor: 15.419

5. Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction.

Authors: Michaelyn C Lux; Melissa L Boby; Joshua L Brooks; Derek S Tan
Journal: Chem Commun (Camb) Date: 2019-05-31 Impact factor: 6.222

10. Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades.

Authors: Brian S Underwood; Jessica Tanuwidjaja; Sze-Sze Ng; Timothy F Jamison
Journal: Tetrahedron Date: 2013-06-24 Impact factor: 2.457

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

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

Review 2. The continuing saga of the marine polyether biotoxins.

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

4. Total Synthesis of the Marine Ladder Polyether Gymnocin B.

5. Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction.

6. Total synthesis of ent-dioxepandehydrothyrsiferol via a bromonium-initiated epoxide-opening cascade.

Review 7. Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades.

Review 8. Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.

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

10. Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades.