Literature DB >> 21247192

Total synthesis of (-)-brevisin: a concise synthesis of a new marine polycyclic ether.

Takefumi Kuranaga1, Naohito Ohtani, Ryosuke Tsutsumi, Daniel G Baden, Jeffrey L C Wright, Masayuki Satake, Kazuo Tachibana.   

Abstract

The first and highly efficient total synthesis of (-)-brevisin has been achieved. The title compound was synthesized in only 29 steps (longest linear sequence) from commercially available starting materials. The synthesis provided over 70 mg of a marine polycyclic ether compound.

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Year:  2011        PMID： 21247192      PMCID： PMC3040829          DOI： 10.1021/ol102925d

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


  10 in total

1.  A new polyether ladder compound produced by the dinoflagellate Karenia brevis.

Authors:  Andrea J Bourdelais; Henry M Jacocks; Jeffrey L C Wright; Paul M Bigwarfe; Daniel G Baden
Journal:  J Nat Prod       Date:  2005-01       Impact factor: 4.050

2.  Total synthesis, structure revision, and absolute configuration of (-)-brevenal.

Authors:  Haruhiko Fuwa; Makoto Ebine; Andrea J Bourdelais; Daniel G Baden; Makoto Sasaki
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

3.  Absolute configuration of brevisamide and brevisin: confirmation of a universal biosynthetic process for Karenia brevis polyethers.

Authors:  Ryan M Van Wagoner; Masayuki Satake; Andrea J Bourdelais; Daniel G Baden; Jeffrey L C Wright
Journal:  J Nat Prod       Date:  2010-06-25       Impact factor: 4.050

4.  Intramolecular Reaction of (gamma-Alkoxyallyl)stannane with Aldehyde: Origin of the Stereoselectivities.

Authors:  Isao Kadota; Miho Kawada; Vladimir Gevorgyan; Yoshinori Yamamoto
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

5.  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
Journal:  J Am Chem Soc       Date:  1986-02-01       Impact factor: 15.419

Review 6.  Convergent strategies for the total synthesis of polycyclic ether marine metabolites.

Authors:  Makoto Sasaki; Haruhiko Fuwa
Journal:  Nat Prod Rep       Date:  2008-01-17       Impact factor: 13.423

7.  Brevisin: an aberrant polycyclic ether structure from the dinoflagellate Karenia brevis and its implications for polyether assembly.

Authors:  Masayuki Satake; Anna Campbell; Ryan M Van Wagoner; Andrea J Bourdelais; Henry Jacocks; Daniel G Baden; Jeffrey L C Wright
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

8.  Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis.

Authors:  Takefumi Kuranaga; Tomohiro Shirai; Daniel G Baden; Jeffrey L C Wright; Masayuki Satake; Kazuo Tachibana
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

9.  Brevisamide: an unprecedented monocyclic ether alkaloid from the dinoflagellate Karenia brevis that provides a potential model for ladder-frame initiation.

Authors:  Masayuki Satake; Andrea J Bourdelais; Ryan M Van Wagoner; Daniel G Baden; Jeffrey L C Wright
Journal:  Org Lett       Date:  2008-07-23       Impact factor: 6.005

Review 10.  Natural and derivative brevetoxins: historical background, multiplicity, and effects.

Authors:  Daniel G Baden; Andrea J Bourdelais; Henry Jacocks; Sophie Michelliza; Jerome Naar
Journal:  Environ Health Perspect       Date:  2005-05       Impact factor: 9.031
  10 in total
  3 in total

1.  Rhodium-catalyzed endo-selective epoxide-opening cascades: formal synthesis of (-)-brevisin.

Authors:  Kurt W Armbrust; Matthew G Beaver; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2015-05-18       Impact factor: 15.419

2.  Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction.

Authors:  Megan L Lanier; Amanda C Kasper; Hyoungsu Kim; Jiyong Hong
Journal:  Org Lett       Date:  2014-04-11       Impact factor: 6.005

Review 3.  Chemodiversity of Brevetoxins and Other Potentially Toxic Metabolites Produced by Karenia spp. and Their Metabolic Products in Marine Organisms.

Authors:  Vincent Hort; Eric Abadie; Nathalie Arnich; Marie-Yasmine Dechraoui Bottein; Zouher Amzil
Journal:  Mar Drugs       Date:  2021-11-24       Impact factor: 5.118
  3 in total

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