Literature DB >> 14624575

Total synthesis of gymnocin-A.

Chihiro Tsukano1, Makoto Sasaki.   

Abstract

A highly convergent total synthesis of gymnocin-A, a cyctotoxic polyether marine natural product, has been achieved. The synthesis features Suzuki-Miyaura coupling of the ABCD and FGHIJKLMN rings, stereoselective introduction of the C17 hydroxyl group, ring-closure of the F ring, and a late-stage incorporation of a 2-methyl-2-butenal side chain.

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Year:  2003        PMID： 14624575     DOI： 10.1021/ja038547b

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

2.  Total synthesis, structure revision, and absolute configuration of (-)-brevenal.

Authors:  Haruhiko Fuwa; Makoto Ebine; Andrea J Bourdelais; Daniel G Baden; Makoto Sasaki
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

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

Review 4.  The development of endo-selective epoxide-opening cascades in water.

Authors:  Christopher J Morten; Jeffery A Byers; Aaron R Van Dyke; Ivan Vilotijevic; Timothy F Jamison
Journal:  Chem Soc Rev       Date:  2009-09-16       Impact factor: 54.564

5.  Forging C(sp3)-C(sp3) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

Authors:  Spencer P Pitre; Nicholas A Weires; Larry E Overman
Journal:  J Am Chem Soc       Date:  2019-01-04       Impact factor: 15.419

6.  Maitotoxin: An Inspiration for Synthesis.

Authors:  K C Nicolaou; Robert J Aversa
Journal:  Isr J Chem       Date:  2011-04       Impact factor: 3.333

7.  Total Synthesis of the Marine Ladder Polyether Gymnocin B.

Authors:  Satapanawat Sittihan; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2019-07-08       Impact factor: 15.419

8.  Three challenges toward the assignment of absolute configuration of gymnocin-B.

Authors:  Katsunori Tanaka; Yasuhiro Itagaki; Masayuki Satake; Hideo Naoki; Takeshi Yasumoto; Koji Nakanishi; Nina Berova
Journal:  J Am Chem Soc       Date:  2005-07-06       Impact factor: 15.419

9.  Inspirations, discoveries, and future perspectives in total synthesis.

Authors:  K C Nicolaou
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

Review 10.  Chemodiversity of Brevetoxins and Other Potentially Toxic Metabolites Produced by Karenia spp. and Their Metabolic Products in Marine Organisms.

Authors:  Vincent Hort; Eric Abadie; Nathalie Arnich; Marie-Yasmine Dechraoui Bottein; Zouher Amzil
Journal:  Mar Drugs       Date:  2021-11-24       Impact factor: 5.118
  10 in total

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