Literature DB >> 17465557

Biomimetic synthesis of the tetracyclic core of berkelic acid.

Jingye Zhou1, Barry B Snider.   

Abstract

Acid-catalyzed condensation of 2,6-dihydroxybenzoic acid 3 with ketal aldehyde 14 in methanol at 25 degrees C, followed by CH2N2 esterification, gave a 4:1:4:1 mixture of diastereomers 15b-18b in 60% yield. Equilibration of this mixture with TFA in CDCl3 provided tetracycle 15b (83% yield) with the complete skeleton of berkelic acid. A similar condensation at 0 degrees C afforded 15b-18b and a reduction product 19b, which was probably formed by a 1,5-hydride shift.

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Year:  2007        PMID： 17465557      PMCID： PMC2527759          DOI： 10.1021/ol0704338

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


  5 in total

1.  Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile.

Authors:  Andrea A Stierle; Donald B Stierle; Kal Kelly
Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

2.  A catalytic approach for the functionalization of C(sp3)-H bonds.

Authors:  Mamoru Tobisu; Naoto Chatani
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-03       Impact factor: 15.336

3.  Room temperature intramolecular hydro-O-alkylation of aldehydes: sp3 C-H functionalization via a Lewis acid catalyzed tandem 1,5-hydride transfer/cyclization.

Authors:  Stefan J Pastine; Dalibor Sames
Journal:  Org Lett       Date:  2005-11-24       Impact factor: 6.005

4.  Silicon-directed oxa-Pictet-Spengler cyclization and an unusual dimerization of 2-trimethylsilanyl tryptophols.

Authors:  Xuqing Zhang; Xiaojie Li; James C Lanter; Zhihua Sui
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

5.  Synthesis and dopaminergic activity of 3-substituted 1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyrans: characterization of an auxiliary binding region in the D1 receptor.

Authors:  M P DeNinno; R Schoenleber; R J Perner; L Lijewski; K E Asin; D R Britton; R MacKenzie; J W Kebabian
Journal:  J Med Chem       Date:  1991-08       Impact factor: 7.446
  5 in total
  4 in total

1.  Synthesis of (-)-berkelic acid.

Authors:  Xiaoxing Wu; Jingye Zhou; Barry B Snider
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  A Cycloaddition Strategy for Use toward Berkelic Acid, an MMP Inhibitor and Potent Anticancer Agent Displaying a Unique Chroman Spiroketal Motif.

Authors:  Yaodong Huang; Thomas R R Pettus
Journal:  Synlett       Date:  2008-05-11       Impact factor: 2.454

3.  Introduction of the (-)-berkelic acid side chain and assignment of the C-22 stereochemistry.

Authors:  Xiaoxing Wu; Jingye Zhou; Barry B Snider
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

4.  A biosynthetically inspired synthesis of (-)-berkelic acid and analogs.

Authors:  Christopher F Bender; Christopher L Paradise; Vincent M Lynch; Francis K Yoshimoto; Jef K De Brabander
Journal:  Tetrahedron       Date:  2018-01-12       Impact factor: 2.457
  4 in total

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