Literature DB >> 18959425

Combinatorial synthesis of the 1,5-polyol system based on cross metathesis: structure revision of amphidinol 3.

Tohru Oishi1, Mitsunori Kanemoto, Respati Swasono, Nobuaki Matsumori, Michio Murata.   

Abstract

Combinatorial synthesis of a 1,5-polyol system corresponding to the C1-C14 unit of amphidinol 3 (AM3) and its diastereomers was achieved via chemoselective cross metathesis as the key step. Comparison of (13)C NMR data of the synthetic specimens with that of AM3 led to a controversy regarding the originally proposed structure. From GC-MS analysis of the degradation product, the absolute configuration at C2 of AM3 has been revised to be R.

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Year:  2008        PMID： 18959425     DOI： 10.1021/ol802168r

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


  12 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

Review 2.  Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

Authors:  Takashi L Suyama; William H Gerwick; Kerry L McPhail
Journal:  Bioorg Med Chem       Date:  2011-06-12       Impact factor: 3.641

3.  Fluorous Mixture Synthesis of Four Stereoisomers of the C21-C40 Fragment of Tetrafibricin.

Authors:  Kai Zhang; Dennis P Curran
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

4.  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

5.  Structure and absolute configuration of karlotoxin-2, an ichthyotoxin from the marine dinoflagellate Karlodinium veneficum.

Authors:  Jiangnan Peng; Allen R Place; Wesley Yoshida; Clemens Anklin; Mark T Hamann
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

6.  The cytotoxic mechanism of karlotoxin 2 (KmTx 2) from Karlodinium veneficum (Dinophyceae).

Authors:  Jonathan R Deeds; Robert E Hoesch; Allen R Place; Joseph P Y Kao
Journal:  Aquat Toxicol       Date:  2014-12-15       Impact factor: 4.964

7.  Synthesis of the bis-tetrahydropyran core of amphidinol 3.

Authors:  Michael T Crimmins; Timothy J Martin; Theodore A Martinot
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

8.  Stereochemical Studies of the Karlotoxin Class Using NMR Spectroscopy and DP4 Chemical-Shift Analysis: Insights into their Mechanism of Action.

Authors:  Amanda L Waters; Joonseok Oh; Allen R Place; Mark T Hamann
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-16       Impact factor: 15.336

9.  HiFSA fingerprinting applied to isomers with near-identical NMR spectra: the silybin/isosilybin case.

Authors:  José G Napolitano; David C Lankin; Tyler N Graf; J Brent Friesen; Shao-Nong Chen; James B McAlpine; Nicholas H Oberlies; Guido F Pauli
Journal:  J Org Chem       Date:  2013-03-05       Impact factor: 4.354

10.  Karlotoxin synthetic studies: concise synthesis of a C(42-63) B-ring tetrahydropyran fragment.

Authors:  Takashi Tomioka; Yusuke Takahashi; Toshihide Maejima; Yuki Yabe; Hiroki Iwata; Mark T Hamann
Journal:  Tetrahedron Lett       Date:  2013-11-01       Impact factor: 2.415
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