Literature DB >> 19639953

Total synthesis of brevisamide.

Olugbeminiyi O Fadeyi1, Craig W Lindsley.   

Abstract

The second total synthesis of Brevisamide, a marine cyclic ether alkaloid from Karenia brevis, is reported. This streamlined synthesis proceeds in 21 steps, 14 steps longest linear sequence, in 5.2% overall yield and features a key SmI(2) reductive cyclization step to access the tetrasubstituted pyran core.

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Year:  2009        PMID： 19639953      PMCID： PMC2838230          DOI： 10.1021/ol9015755

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


  8 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.  Synthesis of 2(1H)-pyrazinone phosphonates via an Arbuzov-type reaction.

Authors:  Jo Alen; Liliana Dobrzańska; Wim M De Borggraeve; Frans Compernolle
Journal:  J Org Chem       Date:  2007-02-02       Impact factor: 4.354

3.  Total Synthesis of Lankacyclinol Generous financial support for this research was provided by the National Institutes of Health (Award no.: GM41560). Additionally, a National Institutes of Health Minority Predoctoral Fellowship (Award no.: GM18547) to G.S.C. is gratefully acknowledged. We also wish to thank Dr. Tsuneaki Hida and Dr. Yoshio Kozai, Takeda Chemical Ltd. (Japan), for providing us with an authentic sample of lankacyclinol as well as copies of the original (1)H NMR spectrum.

Authors:  David R. Williams; Guillermo S. Cortez; Stéphane L. Bogen; Christian M. Rojas
Journal:  Angew Chem Int Ed Engl       Date:  2000-12-15       Impact factor: 15.336

4.  Total synthesis of the proposed structure for pyragonicin.

Authors:  Shunya Takahashi; Narihito Ogawa; Hiroyuki Koshino; Tadashi Nakata
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

5.  Concise enantioselective total synthesis of neopeltolide macrolactone highlighted by ether transfer.

Authors:  Rendy Kartika; Thomas R Gruffi; Richard E Taylor
Journal:  Org Lett       Date:  2008-10-15       Impact factor: 6.005

6.  Total synthesis of brevenal.

Authors:  Hiroyoshi Takamura; Shigetoshi Kikuchi; Yuichi Nakamura; Yuji Yamagami; Takayuki Kishi; Isao Kadota; Yoshinori Yamamoto
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

7.  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

8.  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
  8 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.  A Formal Total Synthesis of (-)-Brevisamide.

Authors:  Amos B Smith; Noriki Kutsumura; Justin Potuzak
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415
  2 in total

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