Literature DB >> 22475318

Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.

Rodolfo Tello-Aburto1, Emily M Johnson, Cheyenne K Valdez, William A Maio.   

Abstract

The first asymmetric total synthesis and determination of the absolute configuration for the neuroactive marine macrolide palmyrolide A is described. The highlight of the synthesis is macrocyclization via trans-enamide formation catalyzed by copper(I) iodide and cesium carbonate. Comparison with the authentic spectral data confirms the synthesis of (+)-ent-palmyrolide A.
© 2012 American Chemical Society

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 22475318      PMCID: PMC3352666          DOI: 10.1021/ol300673m

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


  36 in total

Review 1.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

Authors:  Gwilherm Evano; Nicolas Blanchard; Mathieu Toumi
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

2.  Structures of TMC-95A-D: novel proteasome inhibitors from Apiospora montagnei sacc. TC 1093.

Authors:  J Kohno; Y Koguchi; M Nishio; K Nakao; M Kuroda; R Shimizu; T Ohnuki; S Komatsubara
Journal:  J Org Chem       Date:  2000-02-25       Impact factor: 4.354

3.  A remarkable solvent effect toward the Pd/C-catalyzed cleavage of silyl ethers.

Authors:  Hironao Sajiki; Takashi Ikawa; Kazuyuki Hattori; Kosaku Hirota
Journal:  Chem Commun (Camb)       Date:  2003-03-07       Impact factor: 6.222

4.  Cyclopeptide alkaloids from Paliurus ramossisimus.

Authors:  H Y Lin; C H Chen; B J You; K C Liu; S S Lee
Journal:  J Nat Prod       Date:  2000-10       Impact factor: 4.050

5.  Total synthesis of apratoxin A.

Authors:  Jiehao Chen; Craig J Forsyth
Journal:  J Am Chem Soc       Date:  2003-07-23       Impact factor: 15.419

6.  Copper-catalyzed coupling of amides and carbamates with vinyl halides.

Authors:  Lei Jiang; Gabriel E Job; Artis Klapars; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

7.  Acryloyl chloride: an excellent substrate for cross-metathesis. a one-pot sequence for the synthesis of substituted alpha,beta-unsaturated carbonyl derivatives.

Authors:  Laurent Ferrié; Samir Bouzbouz; Janine Cossy
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

8.  Total synthesis of (-)-apratoxin A, 34-epimer, and its oxazoline analogue.

Authors:  Yoshitaka Numajiri; Takashi Takahashi; Takayuki Doi
Journal:  Chem Asian J       Date:  2009-01-05

9.  Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950.

Authors:  Robert S Coleman; Pei-Hua Liu
Journal:  Org Lett       Date:  2004-02-19       Impact factor: 6.005

10.  CuI/N,N-dimethylglycine-catalyzed coupling of vinyl halides with amides or carbamates.

Authors:  Xianhua Pan; Qian Cai; Dawei Ma
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005

View more
  5 in total

1.  Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates.

Authors:  Meredith S Eno; Alexander Lu; James P Morken
Journal:  J Am Chem Soc       Date:  2016-06-16       Impact factor: 15.419

2.  Total Synthesis and Structural Reassignment of Laingolide A.

Authors:  Fusong Wu; Tao Zhang; Jie Yu; Yian Guo; Tao Ye
Journal:  Mar Drugs       Date:  2021-04-27       Impact factor: 5.118

3.  Detailed analysis of (-)-palmyrolide a and some synthetic derivatives as voltage-gated sodium channel antagonists.

Authors:  Suneet Mehrotra; Brendan M Duggan; Rodolfo Tello-Aburto; Tara D Newar; William H Gerwick; Thomas F Murray; William A Maio
Journal:  J Nat Prod       Date:  2014-10-24       Impact factor: 4.050

Review 4.  The Chemistry, Biochemistry and Pharmacology of Marine Natural Products from Leptolyngbya, a Chemically Endowed Genus of Cyanobacteria.

Authors:  Yueying Li; C Benjamin Naman; Kelsey L Alexander; Huashi Guan; William H Gerwick
Journal:  Mar Drugs       Date:  2020-10-06       Impact factor: 5.118

Review 5.  Shellfish toxins targeting voltage-gated sodium channels.

Authors:  Fan Zhang; Xunxun Xu; Tingting Li; Zhonghua Liu
Journal:  Mar Drugs       Date:  2013-11-28       Impact factor: 5.118

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.