Literature DB >> 19099481

Total synthesis of brevetoxin A.

Michael T Crimmins1, J Lucas Zuccarello, J Michael Ellis, Patrick J McDougall, Pamela A Haile, Jonathan D Parrish, Kyle A Emmitte.   

Abstract

A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.

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Year:  2009        PMID： 19099481      PMCID： PMC2640830          DOI： 10.1021/ol802710u

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


  15 in total

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2.  A convergent coupling strategy for the formation of polycyclic ethers: stereoselective synthesis of the BCDE fragment of brevetoxin A.

Authors:  Michael T Crimmins; Patrick J McDougall; Kyle A Emmitte
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4.  Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A.

Authors:  Michael T Crimmins; J Lucas Zuccarello; Pamela A Cleary; Jonathan D Parrish
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

Review 5.  Convergent strategies for syntheses of trans-fused polycyclic ethers.

Authors:  Masayuki Inoue
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

6.  Improved synthesis of the ABCDE fragment of brevetoxin A.

Authors:  Michael T Crimmins; Patrick J McDougall; J Michael Ellis
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

7.  Synthetic strategies of marine polycyclic ethers via intramolecular allylations: linear and convergent approaches.

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Journal:  Acc Chem Res       Date:  2005-05       Impact factor: 22.384

8.  Structure of brevetoxin A (GB-1 toxin), the most potent toxin in the Florida red tide organism Gymnodinium breve (Ptychodiscus brevis).

Authors:  Y Shimizu; H N Chou; H Bando; G Van Duyne; J Clardy
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9.  Total synthesis of brevetoxin A.

Authors:  K C Nicolaou; Z Yang; G Shi; J L Gunzner; K A Agrios; P Gärtner
Journal:  Nature       Date:  1998-03-19       Impact factor: 49.962

10.  Overview of aerosolized Florida red tide toxins: exposures and effects.

Authors:  Lora E Fleming; Lorraine C Backer; Daniel G Baden
Journal:  Environ Health Perspect       Date:  2005-05       Impact factor: 9.031
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  8 in total

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5.  Review of Florida Red Tide and Human Health Effects.

Authors:  Lora E Fleming; Barbara Kirkpatrick; Lorraine C Backer; Cathy J Walsh; Kate Nierenberg; John Clark; Andrew Reich; Julie Hollenbeck; Janet Benson; Yung Sung Cheng; Jerome Naar; Richard Pierce; Andrea J Bourdelais; William M Abraham; Gary Kirkpatrick; Julia Zaias; Adam Wanner; Eliana Mendes; Stuart Shalat; Porter Hoagland; Wendy Stephan; Judy Bean; Sharon Watkins; Tainya Clarke; Margaret Byrne; Daniel G Baden
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Review 6.  Development of novel drugs from marine surface associated microorganisms.

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7.  Enantioselective total synthesis of brevetoxin A: unified strategy for the B, E, G, and J subunits.

Authors:  Michael T Crimmins; J Michael Ellis; Kyle A Emmitte; Pamela A Haile; Patrick J McDougall; Jonathan D Parrish; J Lucas Zuccarello
Journal:  Chemistry       Date:  2009-09-14       Impact factor: 5.236

8.  Enantioselective total synthesis of brevetoxin A: convergent coupling strategy and completion.

Authors:  Michael T Crimmins; J Lucas Zuccarello; Patrick J McDougall; J Michael Ellis
Journal:  Chemistry       Date:  2009-09-14       Impact factor: 5.236
  8 in total

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