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Literature DB >> 22514791

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

Abstract

This article describes the development of microwave-assisted oxyanionic 5-exo-dig cyclization-Claisen rearrangement sequence as a convenient "one-pot" route to a variety of seven-membered carbocyclic ring systems. This process was used as the key transformation for the construction of several natural products, including frondosins A, B, and C.

Entities: Chemical Disease Gene Species

Year: 2010 PMID： 22514791 PMCID： PMC3327132

Source DB: PubMed Journal: ARKIVOC Impact factor: 1.140

28 in total

1. The Total Synthesis of Frondosin B.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-02 Impact factor: 15.336

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

Authors: T V Ovaska; J B Roses
Journal: Org Lett Date: 2000-07-27 Impact factor: 6.005

Review 3. Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes.

Authors: Francisco Alonso; Irina P Beletskaya; Miguel Yus
Journal: Chem Rev Date: 2004-06 Impact factor: 60.622

4. First approach to the frondosin C ring system via a tandem cyclization/Claisen rearrangement sequence.

Authors: Isamir Martínez; Philip E Alford; Timo V Ovaska
Journal: Org Lett Date: 2005-03-17 Impact factor: 6.005

5. The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings.

Authors: Merle A Battiste; Phillip M Pelphrey; Dennis L Wright
Journal: Chemistry Date: 2006-04-24 Impact factor: 5.236

Review 6. The role of interleukin-8 and its receptors in gliomagenesis and tumoral angiogenesis.

Authors: Daniel J Brat; Anita C Bellail; Erwin G Van Meir
Journal: Neuro Oncol Date: 2005-04 Impact factor: 12.300

7. Dichloromethane activation. Direct methylenation of ketones and aldehydes with CH2Cl2 promoted by Mg/TiCl4/THF.

Authors: Tu-Hsin Yan; Chia-Chung Tsai; Ching-Ting Chien; Chia-Ching Cho; Pei-Chen Huang
Journal: Org Lett Date: 2004-12-23 Impact factor: 6.005

8. Asymmetric [4+3] cycloadditions between benzofuranyldiazoacetates and dienes: formal synthesis of (+)-frondosin B.

Authors: Jeremy P Olson; Huw M L Davies
Journal: Org Lett Date: 2008-01-24 Impact factor: 6.005

9. Studies toward frondosin A and its analogues. Formal total synthesis of (+/-)-frondosin A.

Authors: Xin Li; Alec E Keon; Jonathan A Sullivan; Timo V Ovaska
Journal: Org Lett Date: 2008-07-09 Impact factor: 6.005

10. Enhanced production of neutrophil-activating peptide-1/interleukin-8 in rheumatoid arthritis.

Authors: M Seitz; B Dewald; N Gerber; M Baggiolini
Journal: J Clin Invest Date: 1991-02 Impact factor: 14.808

4 in total

1. Facile Access to Cyclooctanoid Ring Systems via Microwave-Assisted Tandem 6-exo dig Cyclization-Rearrangement Sequence.

Authors: Aaron W Feldman; Sami I Ovaska; Timo V Ovaska
Journal: Tetrahedron Date: 2014-07-08 Impact factor: 2.457