Literature DB >> 10930284

Tandem anionic 5-Exo dig cyclization/Claisen rearrangement as an efficient route to fused polycyclic ring systems.

T V Ovaska1, J B Roses.   

Abstract

The scope and limitations of a tandem 5-exo dig cyclization/Claisen rearrangement sequence involving appropriately substituted 4-alkyn-1-ols as an efficient "one-pot" route to fused tricyclic ring systems is described. The reaction rates were found to be strongly dependent on the nature of the terminal substitutent of the triple bond. In some cases the entire sequence was found to proceed in good yield at temperatures as low as 115 degrees C.

Entities:  

Mesh：

Substances：

Year:  2000        PMID： 10930284     DOI： 10.1021/ol006139w

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


  5 in total

1.  Progress toward the total synthesis of frondosin C.

Authors:  Xin Li; Robert E Kyne; Timo V Ovaska
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

2.  Intramolecular thermal allenyne [2 + 2] cycloadditions; facile construction of the 5-6-4 ring core of sterpurene.

Authors:  Timo V Ovaska; Robert E Kyne
Journal:  Tetrahedron Lett       Date:  2008-01-07       Impact factor: 2.415

3.  Synthesis of cycloheptanoid natural products via tandem 5-exo cyclization/Claisen rearrangement process.

Authors:  Timo V Ovaska
Journal:  ARKIVOC       Date:  2010-10-31       Impact factor: 1.140

4.  Asymmetric synthesis of seven-membered carbocyclic rings via a sequential oxyanionic 5-exo-dig cyclization/claisen rearrangement process. Total synthesis of (-)-frondosin B.

Authors:  Timo V Ovaska; Jonathan A Sullivan; Sami I Ovaska; Jacob B Winegrad; Justin D Fair
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

5.  Synthesis of seven-membered carbocyclic rings via a microwave-assisted tandem oxyanionic 5-exo dig cyclization-claisen rearrangement process.

Authors:  Xin Li; Robert E Kyne; Timo V Ovaska
Journal:  J Org Chem       Date:  2007-07-27       Impact factor: 4.354
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.