Literature DB >> 18389143

Convergent strategies for the total synthesis of polycyclic ether marine metabolites.

Makoto Sasaki1, Haruhiko Fuwa.   

Abstract

Marine polycyclic ether natural products continue to fascinate chemists and biologists due to their exceptionally large and complex molecular architectures and potent and diverse biological activities. Tremendous progress has been made over the past decade toward the total synthesis of marine polycyclic ether natural products. In this area, a convergent strategy for assembling small fragments into an entire molecule always plays a key role in successful total synthesis. This review describes our efforts to develop convergent strategies for the synthesis of polycyclic ethers and their application to the total synthesis of gambierol, gymnocin-A, and brevenal, and to the partial synthesis of the central part of ciguatoxins and the nonacyclic polyether skeleton of gambieric acids.

Entities:  

Mesh:

Substances:

Year:  2008        PMID: 18389143     DOI: 10.1039/b705664h

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  15 in total

1.  Lessons and revelations from biomimetic syntheses.

Authors:  Mina Razzak; Jef K De Brabander
Journal:  Nat Chem Biol       Date:  2011-11-15       Impact factor: 15.040

2.  Hydroxyl-substituted ladder polyethers via selective tandem epoxidation/cyclization sequence.

Authors:  Lara C Czabaniuk; Timothy F Jamison
Journal:  Org Lett       Date:  2015-02-03       Impact factor: 6.005

Review 3.  The continuing saga of the marine polyether biotoxins.

Authors:  K C Nicolaou; Michael O Frederick; Robert J Aversa
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Ladder polyether synthesis via epoxide-opening cascades directed by a disappearing trimethylsilyl group.

Authors:  Timothy P Heffron; Graham L Simpson; Estibaliz Merino; Timothy F Jamison
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

5.  Total synthesis of brevenal.

Authors:  Yuan Zhang; John Rohanna; Jie Zhou; Karthik Iyer; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2011-02-15       Impact factor: 15.419

6.  Total synthesis of (-)-brevisin: a concise synthesis of a new marine polycyclic ether.

Authors:  Takefumi Kuranaga; Naohito Ohtani; Ryosuke Tsutsumi; Daniel G Baden; Jeffrey L C Wright; Masayuki Satake; Kazuo Tachibana
Journal:  Org Lett       Date:  2011-01-19       Impact factor: 6.005

Review 7.  Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades.

Authors:  Ivan Vilotijevic; Timothy F Jamison
Journal:  Mar Drugs       Date:  2010-03-19       Impact factor: 5.118

Review 8.  Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.

Authors:  Ivan Vilotijevic; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  New reactions of 2-methylenetetrahydropyrans. A three component coupling protocol for the synthesis of tetrahydropyranyl ketides.

Authors:  Guohua Liang; Laura J Bateman; Nancy I Totah
Journal:  Chem Commun (Camb)       Date:  2009-09-23       Impact factor: 6.222

10.  Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis.

Authors:  Matthew Katcher; Timothy F Jamison
Journal:  Tetrahedron       Date:  2018-02-02       Impact factor: 2.457

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.