Literature DB >> 18321120

Long-chain 2H-azirines with heterogeneous terminal halogenation from the marine sponge Dysidea fragilis.

Colin K Skepper1, Tadeusz F Molinski.   

Abstract

Three new omega-halogenated long-chain 2H-azirines were isolated from the sponge Dysidea fragilis. Their structures revealed heterogeneity in both the composition of the terminal 1,1-dihalo-vinyl group and enantiomeric ratios at C2 of the azirine-2-carboxylate ester terminus. Azirine-2-carboxylate esters were shown to racemize spontaneously. A hypothesis is proposed for the biosynthesis of the azirinecarboxylate family of natural products that involves enzyme-catalyzed free radical halogenation followed by elimination of hydrohalic acid.

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Year:  2008        PMID： 18321120     DOI： 10.1021/jo702435s

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

1.  Synthesis and chain-dependent antifungal activity of long-chain 2H-azirine-carboxylate esters related to dysidazirine.

Authors:  Colin K Skepper; Doralyn S Dalisay; Tadeusz F Molinski
Journal:  Bioorg Med Chem Lett       Date:  2010-02-01       Impact factor: 2.823

2.  Mollenyne A, a long-chain chlorodibromohydrin amide from the sponge Spirastrella mollis.

Authors:  Brandon I Morinaka; Tadeusz F Molinski
Journal:  Org Lett       Date:  2011-11-16       Impact factor: 6.005

3.  Synthesis and antifungal activity of (-)-(Z)-dysidazirine.

Authors:  Colin K Skepper; Doralyn S Dalisay; Tadeusz F Molinski
Journal:  Org Lett       Date:  2008-10-21       Impact factor: 6.005

4.  Halisphingosines A and B, modified sphingoid bases from Haliclona tubifera. Assignment of configuration by circular dichroism and van't Hoff's principle of optical superposition.

Authors:  Tadeusz F Molinski; Renata Biegelmeyer; E Paige Stout; Xiao Wang; Mario L C Frota; Amelia T Henriques
Journal:  J Nat Prod       Date:  2012-12-26       Impact factor: 4.050

5.  Acremolin from Acremonium strictum is N(2),3-etheno-2'-isopropyl-1-methylguanine, not a 1H-azirine. Synthesis and structural revision.

Authors:  Lawrence A Januar; Tadeusz F Molinski
Journal:  Org Lett       Date:  2013-05-01       Impact factor: 6.005

6.  Absolute configuration of the alpha,omega-bifunctionalized sphingolipid leucettamol A from Leucetta microrhaphis by deconvoluted exciton coupled CD.

Authors:  Doralyn S Dalisay; Sachiko Tsukamoto; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

7.  Motualevic acids A-F, antimicrobial acids from the sponge Siliquariaspongia sp.

Authors:  Jessica L Keffer; Alberto Plaza; Carole A Bewley
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

8.  Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination.

Authors:  Jiyun Sun; Xiaohua Zhen; Huaibin Ge; Guangtao Zhang; Xuechan An; Yunfei Du
Journal:  Beilstein J Org Chem       Date:  2018-06-15       Impact factor: 2.883

9.  Anti-Inflammatory Dysidazirine Carboxylic Acid from the Marine Cyanobacterium Caldora sp. Collected from the Reefs of Fort Lauderdale, Florida.

Authors:  Sarath P Gunasekera; Sofia Kokkaliari; Ranjala Ratnayake; Thomas Sauvage; Larissa A H Dos Santos; Hendrik Luesch; Valerie J Paul
Journal:  Molecules       Date:  2022-03-06       Impact factor: 4.411

Review 10.  The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.

Authors:  James B McAlpine; Shao-Nong Chen; Andrei Kutateladze; John B MacMillan; Giovanni Appendino; Andersson Barison; Mehdi A Beniddir; Maique W Biavatti; Stefan Bluml; Asmaa Boufridi; Mark S Butler; Robert J Capon; Young H Choi; David Coppage; Phillip Crews; Michael T Crimmins; Marie Csete; Pradeep Dewapriya; Joseph M Egan; Mary J Garson; Grégory Genta-Jouve; William H Gerwick; Harald Gross; Mary Kay Harper; Precilia Hermanto; James M Hook; Luke Hunter; Damien Jeannerat; Nai-Yun Ji; Tyler A Johnson; David G I Kingston; Hiroyuki Koshino; Hsiau-Wei Lee; Guy Lewin; Jie Li; Roger G Linington; Miaomiao Liu; Kerry L McPhail; Tadeusz F Molinski; Bradley S Moore; Joo-Won Nam; Ram P Neupane; Matthias Niemitz; Jean-Marc Nuzillard; Nicholas H Oberlies; Fernanda M M Ocampos; Guohui Pan; Ronald J Quinn; D Sai Reddy; Jean-Hugues Renault; José Rivera-Chávez; Wolfgang Robien; Carla M Saunders; Thomas J Schmidt; Christoph Seger; Ben Shen; Christoph Steinbeck; Hermann Stuppner; Sonja Sturm; Orazio Taglialatela-Scafati; Dean J Tantillo; Robert Verpoorte; Bin-Gui Wang; Craig M Williams; Philip G Williams; Julien Wist; Jian-Min Yue; Chen Zhang; Zhengren Xu; Charlotte Simmler; David C Lankin; Jonathan Bisson; Guido F Pauli
Journal:  Nat Prod Rep       Date:  2018-07-13       Impact factor: 13.423
  10 in total

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