Literature DB >> 16321027

Catalytic asymmetric claisen rearrangement in natural product synthesis: synthetic studies toward (-)-xeniolide F.

Annett Pollex1, Martin Hiersemann.   

Abstract

[chemical reaction: see text]. The catalytic asymmetric Claisen rearrangement (CAC) of a highly substituted and functionalized alpha-alkoxycarbonyl-substituted allyl vinyl ether has been exploited to gain access to an advanced building block for the projected total synthesis of (-)-xeniolide F, the enantiomer of a xenicane diterpene isolated from a coral of the genus Xenia.

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Year:  2005        PMID: 16321027     DOI: 10.1021/ol052462t

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


  8 in total

1.  Induction of apoptosis by diterpenes from the soft coral Xenia elongata.

Authors:  Eric H Andrianasolo; Liti Haramaty; Kurt Degenhardt; Robin Mathew; Eileen White; Richard Lutz; Paul Falkowski
Journal:  J Nat Prod       Date:  2007-09-28       Impact factor: 4.050

2.  (3R,4S,5S)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]tetra-hydro-furan-2-one.

Authors:  Annika Becker; Markus Schürmann; Hans Preut; Martin Hiersemann
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-07-16

3.  Reactions of nitroso hetero-Diels-Alder cycloadducts with azides: stereoselective formation of triazolines and aziridines.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  J Org Chem       Date:  2007-04-13       Impact factor: 4.354

4.  (3S,4S,5S)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]-4,5-dihydro-furan-2(3H)-one.

Authors:  Annika Gille; Markus Schürmann; Hans Preut; Martin Hiersemann
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-08-30

5.  (3S,4S,5R)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]-4,5-dihydro-furan-2(3H)-one.

Authors:  Annika Gille; Dieter Bläser; Roland Boese; Hans Preut; Martin Hiersemann
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-17

6.  {2,2-Bis[(4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]propane}-bis-(N,N-dimethyl-formamide)-copper(II) bis-[hexa-fluoridoanti-monate(V)].

Authors:  Julia Zeh; Melina Möller; Carsten Strohmann; Hans Preut; Martin Hiersemann
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-27

7.  Mode of action of diterpene and characterization of related metabolites from the soft coral, Xenia elongata.

Authors:  Eric H Andrianasolo; Liti Haramaty; Eileen White; Richard Lutz; Paul Falkowski
Journal:  Mar Drugs       Date:  2014-02-20       Impact factor: 5.118

Review 8.  Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms.

Authors:  Tatjana Huber; Lara Weisheit; Thomas Magauer
Journal:  Beilstein J Org Chem       Date:  2015-12-10       Impact factor: 2.883

  8 in total

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