Literature DB >> 19140150

Synthesis of (-)-berkelic acid.

Xiaoxing Wu1, Jingye Zhou, Barry B Snider.   

Abstract

An extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6-dihydroxybenzoic acid is the key step in the synthesis of (-)-berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.

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Year:  2009        PMID： 19140150      PMCID： PMC2790819          DOI： 10.1002/anie.200805488

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


  11 in total

1.  Toward globular macromolecules with functionalized interiors: design and synthesis of dendrons with an interesting twist.

Authors:  P Bharathi; H Zhao; S Thayumanavan
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

2.  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

3.  A synthesis-driven structure revision of berkelic acid methyl ester.

Authors:  Philipp Buchgraber; Thomas N Snaddon; Conny Wirtz; Richard Mynott; Richard Goddard; Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)Co(III) complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols.

Authors:  Scott E Schaus; Bridget D Brandes; Jay F Larrow; Makoto Tokunaga; Karl B Hansen; Alexandra E Gould; Michael E Furrow; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2002-02-20       Impact factor: 15.419

5.  Asymmetric conjugate additions of chiral phosphonamide anions to alpha,beta-unsaturated carbonyl compounds. A versatile method for vicinally substituted chirons

Authors: 
Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

6.  A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions.

Authors:  Mostofa A. Hena
Journal:  J Org Chem       Date:  1999-07-23       Impact factor: 4.354

7.  Powerful Ti-crossed Claisen condensation between ketene silyl acetals or thioacetals and acid chlorides or acids.

Authors:  Akira Iida; Syogo Nakazawa; Tomohito Okabayashi; Atsushi Horii; Tomonori Misaki; Yoo Tanabe
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005

8.  Diastereoselective syntheses of chroman spiroketals via [4 + 2] cycloaddition of enol ethers and o-quinone methides.

Authors:  Maurice A Marsini; Yaodong Huang; Christopher C Lindsey; Kun-Liang Wu; Thomas R R Pettus
Journal:  Org Lett       Date:  2008-03-13       Impact factor: 6.005

9.  Biomimetic synthesis of the tetracyclic core of berkelic acid.

Authors:  Jingye Zhou; Barry B Snider
Journal:  Org Lett       Date:  2007-04-28       Impact factor: 6.005

10.  Regulated-stereoselective construction of thirteen stereogenic centers necessary for the frame of (+)-discodermolide, based on iterative Lewis acid-promoted aldol reactions.

Authors:  Syun-ichi Kiyooka; Kazi Abdus Shahid; Fumitaka Goto; Momotoshi Okazaki; Yoshihiro Shuto
Journal:  J Org Chem       Date:  2003-10-17       Impact factor: 4.354
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  11 in total

1.  Lessons and revelations from biomimetic syntheses.

Authors:  Mina Razzak; Jef K De Brabander
Journal:  Nat Chem Biol       Date:  2011-11-15       Impact factor: 15.040

2.  A diastereoselective formal synthesis of berkelic acid.

Authors:  Todd A Wenderski; Maurice A Marsini; Thomas R R Pettus
Journal:  Org Lett       Date:  2010-12-07       Impact factor: 6.005

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.  Stereoselective synthesis of benzannulated spiroketals: influence of the aromatic ring on reactivity and conformation.

Authors:  Guodong Liu; Jacqueline M Wurst; Derek S Tan
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

5.  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

6.  A concise synthesis of berkelic acid inspired by combining the natural products spicifernin and pulvilloric acid.

Authors:  Christopher F Bender; Francis K Yoshimoto; Christopher L Paradise; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419

7.  A Revised Modular Approach to (-)-trans-Δ8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions.

Authors:  Victor R L J Bloemendal; Daan Sondag; Hidde Elferink; Thomas J Boltje; Jan C M van Hest; Floris P J T Rutjes
Journal:  European J Org Chem       Date:  2019-03-18

8.  Solvent-dependent divergent functions of Sc(OTf)₃ in stereoselective epoxide-opening spiroketalizations.

Authors:  Indrajeet Sharma; Jacqueline M Wurst; Derek S Tan
Journal:  Org Lett       Date:  2014-04-17       Impact factor: 6.005

Review 9.  Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules.

Authors:  Thilo Focken; Stephen Hanessian
Journal:  Beilstein J Org Chem       Date:  2014-08-13       Impact factor: 2.883

Review 10.  Marine-Derived Penicillium Species as Producers of Cytotoxic Metabolites.

Authors:  Sen Liu; Mingzhi Su; Shao-Jiang Song; Jee H Jung
Journal:  Mar Drugs       Date:  2017-10-24       Impact factor: 5.118
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