Literature DB >> 24376284

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

Takashi Tomioka1, Yusuke Takahashi1, Toshihide Maejima1, Yuki Yabe1, Hiroki Iwata1, Mark T Hamann2.   

Abstract

Starting from natural D-mannose, a C(42-63) B-ring tetrahydropyran fragment in karlotoxin 2 has been prepared via a common THP intermediate in a concise manner. E-selective Julia-Kocienski olefination efficiently assembled a C(51-63) chlorodiene subunit and a C(42-50) tetrahydropyran segment.

Entities:  

Keywords:  D-Mannose; Julia-Kocienski olefination; Karlotoxin; Polyketide; Tetrahydropyran

Year:  2013        PMID： 24376284      PMCID： PMC3873160          DOI： 10.1016/j.tetlet.2013.09.104

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  20 in total

1.  A C-glycosidation approach to the central core of amphidinol 3: synthesis of the c39-c52 fragment.

Authors:  Javier de Vicente; Bodo Betzemeier; Scott D Rychnovsky
Journal:  Org Lett       Date:  2005-04-28       Impact factor: 6.005

2.  Development of an access route to the c31-c52 central core of amphidinol 3.

Authors:  Matthew W Bedore; Shuh-Kuen Chang; Leo A Paquette
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

3.  Synthesis of the C(26)-C(42) and C(43)-C(67) pyran-containing fragments of amphidinol 3 via a common pyran intermediate.

Authors:  Jacqueline D Hicks; William R Roush
Journal:  Org Lett       Date:  2008-01-19       Impact factor: 6.005

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

Authors:  Tohru Oishi; Mitsunori Kanemoto; Respati Swasono; Nobuaki Matsumori; Michio Murata
Journal:  Org Lett       Date:  2008-10-30       Impact factor: 6.005

5.  Automated high-throughput synthesis of artificial glycopeptides. Small-molecule probes for chemical glycobiology.

Authors:  Prabhat Arya; Angela Barkley; Karla D Randell
Journal:  J Comb Chem       Date:  2002 May-Jun

6.  Synthesis of the C(43)-C(67) fragment of amphidinol 3.

Authors:  Jacqueline D Hicks; Eric M Flamme; William R Roush
Journal:  Org Lett       Date:  2005-11-24       Impact factor: 6.005

7.  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

8.  Stereoselective chemical synthesis of sugar nucleotides via direct displacement of acylated glycosyl bromides.

Authors:  Shannon C Timmons; David L Jakeman
Journal:  Org Lett       Date:  2007-03-06       Impact factor: 6.005

9.  Diastereoselective synthesis of the C17-C30 fragment of amphidinol 3.

Authors:  Nicolas Rival; Damien Hazelard; Gilles Hanquet; Thomas Kreuzer; Charlelie Bensoussan; Sébastien Reymond; Janine Cossy; Françoise Colobert
Journal:  Org Biomol Chem       Date:  2012-10-30       Impact factor: 3.876

10.  Synthesis and structure revision of the C43-C67 part of amphidinol 3.

Authors:  Makoto Ebine; Mitsunori Kanemoto; Yoshiyuki Manabe; Yosuke Konno; Ken Sakai; Nobuaki Matsumori; Michio Murata; Tohru Oishi
Journal:  Org Lett       Date:  2013-05-21       Impact factor: 6.005
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