Literature DB >> 21572531

A Formal Total Synthesis of (-)-Brevisamide.

Amos B Smith1, Noriki Kutsumura, Justin Potuzak.   

Abstract

A formal total synthesis of (-)-brevisamide has been achieved. The synthetic approach highlights a chemoselective asymmetric dihydroxylation and a one-pot Fraser-Reid epoxidation/PMB protection reaction sequence.

Entities:  

Year:  2011        PMID： 21572531      PMCID： PMC3092486          DOI： 10.1016/j.tetlet.2010.11.013

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


  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.  A concise total synthesis of melithiazole C.

Authors:  Julian Gebauer; Stellios Arseniyadis; Janine Cossy
Journal:  Org Lett       Date:  2007-07-18       Impact factor: 6.005

3.  1,4,7-Trimethyloxatriquinane: S(N)2 reaction at tertiary carbon.

Authors:  Mark Mascal; Nema Hafezi; Michael D Toney
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

4.  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

5.  An asymmetric total synthesis of brevisamide.

Authors:  Arun K Ghosh; Jianfeng Li
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

6.  Total synthesis of brevisamide.

Authors:  Olugbeminiyi O Fadeyi; Craig W Lindsley
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

7.  Total synthesis of brevisamide.

Authors:  Jihoon Lee; James S Panek
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

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
  2 in total

1.  A concise asymmetric total synthesis of (+)-brevisamide.

Authors:  Aaron T Herrmann; Steven R Martinez; Armen Zakarian
Journal:  Org Lett       Date:  2011-06-16       Impact factor: 6.005

2.  Calpain inhibition reduces structural and functional impairment of retinal ganglion cells in experimental optic neuritis.

Authors:  Amena W Smith; Baerbel Rohrer; Lee Wheless; Supriti Samantaray; Swapan K Ray; Jun Inoue; Mitsuyoshi Azuma; Naren L Banik
Journal:  J Neurochem       Date:  2016-09-27       Impact factor: 5.546
  2 in total

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