Literature DB >> 15987203

Total synthesis of (+)-dactylolide.

Carina C Sanchez1, Gary E Keck.   

Abstract

[reaction: see text] The development of an approach leading to the total synthesis of dactylolide is described. The key features of this route include a catalytic asymmetric allylation, a diastereoselective pyran annulation, and a Horner-Wadsworth-Emmons macrocyclization.

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Year:  2005        PMID： 15987203      PMCID： PMC1480405          DOI： 10.1021/ol051040g

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


  8 in total

1.  Total synthesis of (+)-zampanolide.

Authors:  A B Smith; I G Safonov; R M Corbett
Journal:  J Am Chem Soc       Date:  2001-12-12       Impact factor: 15.419

2.  Total synthesis of (+)-dactylolide.

Authors:  Amos B Smith; Igor G Safonov
Journal:  Org Lett       Date:  2002-02-21       Impact factor: 6.005

3.  Diastereoselective synthesis of the C(17)-C(28) fragment (the C-D spiroketal unit) of spongistatin 1 (altohyrtin A) via a kinetically controlled iodo-spiroketalization reaction.

Authors:  Edward B Holson; William R Roush
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

4.  Total synthesis of (+)-dactylolide through an efficient sequential Peterson olefination and Prins cyclization reaction.

Authors:  Danielle L Aubele; Shuangyi Wan; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-30       Impact factor: 15.336

5.  An expedient total synthesis of (-)-dactylolide and formal synthesis of (-)-zampanolide.

Authors:  Fei Ding; Michael P Jennings
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

6.  Catalytic asymmetric allylation reactions using BITIP catalysis and 2-substituted allylstannanes as surrogates for beta-keto ester dianions.

Authors:  G E Keck; T Yu
Journal:  Org Lett       Date:  1999-07-29       Impact factor: 6.005

7.  Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

Authors:  Gary E Keck; Jonathan A Covel; Tobias Schiff; Tao Yu
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

8.  Macrolactonization via Ti(IV)-mediated epoxy-acid coupling: a total synthesis of (-)-dactylolide [and zampanolide].

Authors:  Thomas R Hoye; Min Hu
Journal:  J Am Chem Soc       Date:  2003-08-13       Impact factor: 15.419
  8 in total
  14 in total

1.  Mechanistic Analysis of Oxidative C-H Cleavages Using Inter- and Intramolecular Kinetic Isotope Effects.

Authors:  Hyung Hoon Jung; Paul E Floreancig
Journal:  Tetrahedron       Date:  2009-12-26       Impact factor: 2.457

2.  Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.

Authors:  Matthew R Wilson; Richard E Taylor
Journal:  Org Lett       Date:  2012-06-21       Impact factor: 6.005

3.  Studies Toward the Synthesis of (-)-Zampanolide: Preparation of the Macrocyclic Core.

Authors:  Dawn M Troast; Jiayi Yuan; John A Porco
Journal:  Adv Synth Catal       Date:  2008-07-09       Impact factor: 5.837

Review 4.  Microtubule stabilizing agents as potential treatment for Alzheimer's disease and related neurodegenerative tauopathies.

Authors:  Carlo Ballatore; Kurt R Brunden; Donna M Huryn; John Q Trojanowski; Virginia M-Y Lee; Amos B Smith
Journal:  J Med Chem       Date:  2012-09-28       Impact factor: 7.446

5.  Synthesis, conformational preferences, and biological activity of conformational analogues of the microtubule-stabilizing agents, (-)-zampanolide and (-)-dactylolide.

Authors:  Jeffrey L Henry; Matthew R Wilson; Michael P Mulligan; Taylor R Quinn; Dan L Sackett; Richard E Taylor
Journal:  Medchemcomm       Date:  2019-04-09       Impact factor: 3.597

6.  Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent.

Authors:  Arun K Ghosh; Xu Cheng
Journal:  Org Lett       Date:  2011-07-12       Impact factor: 6.005

7.  Optimized synthesis and antiproliferative activity of desTHPdactylolides.

Authors:  Guanglin Chen; Rubing Wang; Bao Vue; Manee Patanapongpibul; Qiang Zhang; Shilong Zheng; Guangdi Wang; James D White; Qiao-Hong Chen
Journal:  Bioorg Med Chem       Date:  2018-05-18       Impact factor: 3.641

8.  Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations.

Authors:  M Paola Castaldi; Dawn M Troast; John A Porco
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

9.  Total Synthesis of Potent Antitumor Macrolide, (-)-Zampanolide: An Oxidative Intramolecular Cyclization-Based Strategy.

Authors:  Arun K Ghosh; Xu Cheng; Ruoli Bai; Ernest Hamel
Journal:  European J Org Chem       Date:  2012-07-01

Review 10.  Macrocyclic drugs and synthetic methodologies toward macrocycles.

Authors:  Xufen Yu; Dianqing Sun
Journal:  Molecules       Date:  2013-05-24       Impact factor: 4.411
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