Literature DB >> 21138313

A diastereoselective formal synthesis of berkelic acid.

Todd A Wenderski1, Maurice A Marsini, Thomas R R Pettus.   

Abstract

A formal synthesis of berkelic acid is reported. The strategy employs the combination of a chiral exocyclic enol ether and an achiral isochromanone to afford the chroman spiroketal core via a base-triggered generation and cycloaddition of an o-quinone methide intermediate. Other key steps include equilibration of the spiroketal, intramolecular benzylic oxidation, and lactone addition/hemiketal reduction; all occur with good diastereoselectivity.

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Year:  2010        PMID： 21138313      PMCID： PMC3107127          DOI： 10.1021/ol102652t

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


  17 in total

1.  A mild anionic method for generating o-quinone methides: facile preparations of ortho-functionalized phenols.

Authors:  R M Jones; R W Van De Water; C C Lindsey; C Hoarau; T Ung; T R Pettus
Journal:  J Org Chem       Date:  2001-05-18       Impact factor: 4.354

Review 2.  Matrix metalloproteinases in cancer.

Authors:  Yoshifumi Itoh; Hideaki Nagase
Journal:  Essays Biochem       Date:  2002       Impact factor: 8.000

Review 3.  Isolation, biological activity and synthesis of benzannulated spiroketal natural products.

Authors:  Jonathan Sperry; Zoe E Wilson; Dominea C K Rathwell; Margaret A Brimble
Journal:  Nat Prod Rep       Date:  2010-03-04       Impact factor: 13.423

4.  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

5.  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

6.  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

7.  Total synthesis of berkelic acid.

Authors:  Thomas N Snaddon; Philipp Buchgraber; Saskia Schulthoff; Conny Wirtz; Richard Mynott; Alois Fürstner
Journal:  Chemistry       Date:  2010-10-25       Impact factor: 5.236

Review 8.  Antibiotics for emerging pathogens.

Authors:  Michael A Fischbach; Christopher T Walsh
Journal:  Science       Date:  2009-08-28       Impact factor: 47.728

9.  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

10.  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
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  11 in total

1.  Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.

Authors:  Thomas J Purgett; Matthew W Dyer; Bryce Bickel; James McNeely; John A Porco
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

2.  New strategies for natural products containing chroman spiroketals.

Authors:  Jason C Green; G Leslie Burnett; Thomas R R Pettus
Journal:  Pure Appl Chem       Date:  2012       Impact factor: 2.453

3.  Multicomponent Condensation Reactions via ortho-Quinone Methides.

Authors:  Emily E Allen; Calvin Zhu; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

4.  Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.

Authors:  Lauren M Chapman; Jordan C Beck; Caitlin R Lacker; Linglin Wu; Sarah E Reisman
Journal:  J Org Chem       Date:  2018-05-18       Impact factor: 4.354

5.  Synthesis of many different types of organic small molecules using one automated process.

Authors:  Junqi Li; Steven G Ballmer; Eric P Gillis; Seiko Fujii; Michael J Schmidt; Andrea M E Palazzolo; Jonathan W Lehmann; Greg F Morehouse; Martin D Burke
Journal:  Science       Date:  2015-03-13       Impact factor: 47.728

6.  Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

Authors:  Ping Lu; Zhenhua Gu; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2013-09-23       Impact factor: 15.419

7.  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

8.  The domestication of ortho-quinone methides.

Authors:  Wen-Ju Bai; Jonathan G David; Zhen-Gao Feng; Marisa G Weaver; Kun-Liang Wu; Thomas R R Pettus
Journal:  Acc Chem Res       Date:  2014-12-03       Impact factor: 22.384

9.  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 10.  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
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