Literature DB >> 23826676

An efficient synthesis of the fully elaborated isoindolinone unit of muironolide A.

Qing Xiao1, Kyle Young, Armen Zakarian.   

Abstract

An efficient stereocontrolled construction of the fully substituted isoindolone subunit of muironolide A is described. The approach is centered on the intramolecular Diels-Alder reaction between the enol form of the β-keto amide and an α,β,γ,δ-unsaturated ester, followed by the installation of the cyclohexene double bond.

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Year:  2013        PMID： 23826676      PMCID： PMC3733332          DOI： 10.1021/ol401354a

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


  19 in total

1.  The Type 2 Intramolecular Diels-Alder Reaction: Synthesis and Chemistry of Bridgehead Alkenes.

Authors:  Brian R. Bear; Steven M. Sparks; Kenneth J. Shea
Journal:  Angew Chem Int Ed Engl       Date:  2001-03-02       Impact factor: 15.336

2.  Tandem Dielsminus signAlder Cycloadditions in Organic Synthesis.

Authors:  Jeffrey D. Winkler
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

3.  Toward the synthesis of norzoanthamine: building carbocyclic core by a transannular Michael reaction cascade.

Authors:  Haoran Xue; Jiong Yang; Peddabuddi Gopal
Journal:  Org Lett       Date:  2011-09-30       Impact factor: 6.005

Review 4.  Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Authors:  Ken-Ichi Takao; Ryosuke Munakata; Kin-ichi Tadano
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

5.  Asymmetric synthesis of salvinorin A, a potent kappa opioid receptor agonist.

Authors:  Jonathan R Scheerer; Jonathan F Lawrence; Grace C Wang; David A Evans
Journal:  J Am Chem Soc       Date:  2007-06-30       Impact factor: 15.419

Review 6.  Recent applications of intramolecular Diels-Alder reactions to natural product synthesis.

Authors:  Martin Juhl; David Tanner
Journal:  Chem Soc Rev       Date:  2009-07-29       Impact factor: 54.564

Review 7.  NMR of natural products at the 'nanomole-scale'.

Authors:  Tadeusz F Molinski
Journal:  Nat Prod Rep       Date:  2010-02-08       Impact factor: 13.423

8.  Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.

Authors:  Romulo Araoz; Denis Servent; Jordi Molgó; Bogdan I Iorga; Carole Fruchart-Gaillard; Evelyne Benoit; Zhenhua Gu; Craig Stivala; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2011-06-17       Impact factor: 15.419

9.  Deslongchamps annulations with benzoquinone monoketals.

Authors:  Denis Petrović; Reinhard Brückner
Journal:  Org Lett       Date:  2011-11-15       Impact factor: 6.005

10.  A tetrachloro polyketide hexahydro-1H-isoindolone, muironolide A, from the marine sponge Phorbas sp. natural products at the nanomole scale.

Authors:  Doralyn S Dalisay; Brandon I Morinaka; Colin K Skepper; Tadeusz F Molinski
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419
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  3 in total

1.  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

Review 2.  The chemistry of isoindole natural products.

Authors:  Klaus Speck; Thomas Magauer
Journal:  Beilstein J Org Chem       Date:  2013-10-10       Impact factor: 2.883

3.  Enantioselective synthesis of (-)-maoecrystal V by enantiodetermining C-H functionalization.

Authors:  Ping Lu; Artur Mailyan; Zhenhua Gu; David M Guptill; Hengbin Wang; Huw M L Davies; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2014-12-11       Impact factor: 15.419
  3 in total

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