Literature DB >> 16706528

Total synthesis of (-)-mucocin.

Michael T Crimmins1, Yan Zhang, Frank A Diaz.   

Abstract

[reaction: see text] An enantioselective total synthesis of (-)-mucocin has been completed. A combination of asymmetric glycolate aldol additions and ring closing metathesis reactions were exploited to construct the C18-C34 and C7-C17 fragments. A selective cross-metathesis reaction was employed as the key step to couple two complex fragments.

Entities:  

Mesh:

Substances:

Year:  2006        PMID: 16706528      PMCID: PMC2546581          DOI: 10.1021/ol060704z

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


  15 in total

Review 1.  Annonaceous acetogenins: recent progress.

Authors:  F Q Alali; X X Liu; J L McLaughlin
Journal:  J Nat Prod       Date:  1999-03       Impact factor: 4.050

2.  Enantioselective total synthesis of (+)-gigantecin: exploiting the asymmetric glycolate aldol reaction.

Authors:  Michael T Crimmins; Jin She
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

Review 3.  Recent advances in Annonaceous acetogenins.

Authors:  L Zeng; Q Ye; N H Oberlies; G Shi; Z M Gu; K He; J L McLaughlin
Journal:  Nat Prod Rep       Date:  1996-08       Impact factor: 13.423

Review 4.  Annonaceous acetogenins: a review.

Authors:  J K Rupprecht; Y H Hui; J L McLaughlin
Journal:  J Nat Prod       Date:  1990 Mar-Apr       Impact factor: 4.050

5.  Synthesis of the non-classical acetogenin mucocin: a modular approach based on olefinic coupling reactions.

Authors:  Lei Zhu; David R Mootoo
Journal:  Org Biomol Chem       Date:  2005-06-30       Impact factor: 3.876

6.  Relay ring-closing metathesis (RRCM): a strategy for directing metal movement throughout olefin metathesis sequences.

Authors:  Thomas R Hoye; Christopher S Jeffrey; Manomi A Tennakoon; Jizhou Wang; Hongyu Zhao
Journal:  J Am Chem Soc       Date:  2004-08-25       Impact factor: 15.419

7.  Synthesis of nonadjacently linked tetrahydrofurans: an iodoetherification and olefin metathesis approach.

Authors:  Lei Zhu; David R Mootoo
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

8.  Mode of action of bullatacin, a potent antitumor acetogenin: inhibition of NADH oxidase activity of HeLa and HL-60, but not liver, plasma membranes.

Authors:  D J Morré; R de Cabo; C Farley; N H Oberlies; J L McLaughlin
Journal:  Life Sci       Date:  1995       Impact factor: 5.037

9.  Mode of action of bullatacin: a potent antitumor and pesticidal annonaceous acetogenin.

Authors:  K I Ahammadsahib; R M Hollingworth; J P McGovren; Y H Hui; J L McLaughlin
Journal:  Life Sci       Date:  1993       Impact factor: 5.037

10.  Enantioselective total synthesis of the potent antitumor agent (-)-mucocin using a temporary silicon-tethered ring-closing metathesis cross-coupling reaction.

Authors:  P Andrew Evans; Jian Cui; Santosh J Gharpure; Alexei Polosukhin; Hai-Ren Zhang
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419

View more
  9 in total

1.  Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

Authors:  John P Wolfe; Michael B Hay
Journal:  Tetrahedron       Date:  2007-01-08       Impact factor: 2.457

2.  Non-natural acetogenin analogues as potent Trypanosoma brucei inhibitors.

Authors:  Gordon J Florence; Andrew L Fraser; Eoin R Gould; Elizabeth F B King; Stefanie K Menzies; Joanne C Morris; Lindsay B Tulloch; Terry K Smith
Journal:  ChemMedChem       Date:  2014-08-21       Impact factor: 3.466

3.  Asymmetric total synthesis of pyranicin.

Authors:  Michael T Crimmins; Danielle L Jacobs
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

4.  Synthesis and antitumor activity of C-9 epimers of the tetrahydrofuran containing acetogenin 4-deoxyannoreticuin.

Authors:  Feng Wang; Akira Kawamura; David R Mootoo
Journal:  Bioorg Med Chem       Date:  2008-08-19       Impact factor: 3.641

5.  A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins.

Authors:  Qiuzhe Xie; Richard W Denton; Kathlyn A Parker
Journal:  Org Lett       Date:  2008-12-04       Impact factor: 6.005

6.  Synthesis and stereochemical assignment of (+)-chamuvarinin.

Authors:  Gordon J Florence; Joanne C Morris; Ross G Murray; Jonathan D Osler; Vanga R Reddy; Terry K Smith
Journal:  Org Lett       Date:  2010-12-21       Impact factor: 6.005

7.  Total synthesis of annonaceous acetogenins belonging to the non-adjacent bis-THF and non-adjacent THF-THP sub-classes.

Authors:  Ian B Spurr; Richard C D Brown
Journal:  Molecules       Date:  2010-01-21       Impact factor: 4.411

8.  Recent progress on the total synthesis of acetogenins from Annonaceae.

Authors:  Nianguang Li; Zhihao Shi; Yuping Tang; Jianwei Chen; Xiang Li
Journal:  Beilstein J Org Chem       Date:  2008-12-05       Impact factor: 2.883

9.  Evolution of catalytic stereoselective olefin metathesis: from ancillary transformation to purveyor of stereochemical identity.

Authors:  Amir H Hoveyda
Journal:  J Org Chem       Date:  2014-04-10       Impact factor: 4.354

  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.