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Literature DB >> 21898738

Synthesis of a bicyclobutane fatty acid identified from the cyanobacterium Anabaena PCC 7120.

Sean M DeGuire¹, Shutao Ma, Gary A Sulikowski.

Abstract

By design: a carbanion-mediated cyclization reaction cascade serves as the key final step in the total synthesis of a novel oxylipin, which features a strained bicyclo[1.1.0]butane conjugated to a labile vinyl epoxide.

Entities: Chemical Species

Mesh：

Substances：
Fatty Acids

Year: 2011 PMID： 21898738 PMCID： PMC4096701 DOI： 10.1002/anie.201104366

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

14 in total

1. Domino Reactions in Organic Synthesis.

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Review 2. The lipoxygenase pathway.

Authors: Ivo Feussner; Claus Wasternack
Journal: Annu Rev Plant Biol Date: 2002 Impact factor: 26.379

Review 3. Oxylipin pathway to jasmonates: biochemistry and biological significance.

Authors: M Hamberg; H W Gardner
Journal: Biochim Biophys Acta Date: 1992-11-11

4. Three-membered-ring-based molecular architectures.

Authors: Armin de Meijere; Sergei I Kozhushkov; Heiko Schill
Journal: Chem Rev Date: 2006-12 Impact factor: 60.622

Review 5. Cascade reactions in total synthesis.

Authors: K C Nicolaou; David J Edmonds; Paul G Bulger
Journal: Angew Chem Int Ed Engl Date: 2006-11-06 Impact factor: 15.336

6. Unsubstituted bicyclo[1.1.0]but-2-ylcarbinyl cations.

Authors: T William Bentley; Bernd Engels; Thomas Hupp; Elena Bogdan; Manfred Christl
Journal: J Org Chem Date: 2006-02-03 Impact factor: 4.354

7. Enzymatic synthesis of a bicyclobutane fatty acid by a hemoprotein lipoxygenase fusion protein from the cyanobacterium Anabaena PCC 7120.

Authors: Claus Schneider; Katrin Niisuke; William E Boeglin; Markus Voehler; Donald F Stec; Ned A Porter; Alan R Brash
Journal: Proc Natl Acad Sci U S A Date: 2007-11-19 Impact factor: 11.205

Review 8. Biosynthesis of oxylipins in non-mammals.

Authors: Alexandra Andreou; Florian Brodhun; Ivo Feussner
Journal: Prog Lipid Res Date: 2009-03-05 Impact factor: 16.195

9. Isolation and characterization of natural allene oxides: unstable intermediates in the metabolism of lipid hydroperoxides.

Authors: A R Brash; S W Baertschi; C D Ingram; T M Harris
Journal: Proc Natl Acad Sci U S A Date: 1988-05 Impact factor: 11.205

Review 10. Beyond prostaglandins--chemistry and biology of cyclic oxygenated metabolites formed by free-radical pathways from polyunsaturated fatty acids.

Authors: Ullrich Jahn; Jean-Marie Galano; Thierry Durand
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

1 in total

1. One-Pot Synthesis of Strain-Release Reagents from Methyl Sulfones.

Authors: Myunggi Jung; Vincent N G Lindsay
Journal: J Am Chem Soc Date: 2022-03-14 Impact factor: 16.383

1 in total