Literature DB >> 12074661

Synthesis of the ABC ring system of azaspiracid. 1. Effect of D ring truncation on bis-spirocyclization.

Rich G Carter1, T Campbell Bourland, David E Graves.   

Abstract

[reaction: see text] Synthesis of a spirocyclization precursor with a truncated D ring has been accomplished. Subsequent bis-spirocyclization induced the formation of equal amounts of the natural transoidal 10R,13R bis-spirocycle and its cisoidal 10R,13S epimer under an apparent thermodynamically controlled process.

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Year:  2002        PMID： 12074661      PMCID： PMC2424237          DOI： 10.1021/ol026033w

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


  10 in total

1.  Synthesis of the FGHI Ring System of Azaspiracid We thank Dr. D. H. Huang and Dr. G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. Financial support for this work was provided by The Skaggs Institute for Chemical Biology, the National Institutes of Health (USA), a predoctoral fellowship from Bristol-Myers Squibb (F.B.), postdoctoral fellowships from the Academy of Finland, the Ella and Georg Ehrnrooth Foundation, and the Tauno Tönning Foundation (all to P.M.P.), ArrayBiopharma (N.Z.), and Bayer AG (N.D.), and grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-LaRoche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.

Authors:  K. C. Nicolaou; Petri M. Pihko; Nicole Diedrichs; Ning Zou; Federico Bernal
Journal:  Angew Chem Int Ed Engl       Date:  2001-04-01       Impact factor: 15.336

2.  Multiple organ damage caused by a new toxin azaspiracid, isolated from mussels produced in Ireland.

Authors:  E Ito; M Satake; K Ofuji; N Kurita; T McMahon; K James; T Yasumoto
Journal:  Toxicon       Date:  2000-07       Impact factor: 3.033

3.  Synthesis of the (+)-C26-C40 Domain of the Azaspiracids by a Novel Double Intramolecular Hetero-Michael Addition Strategy This work was supported by the United States National Institute of Environmental Health Sciences (NIEHS; grant number ES10615), NIH, and by Bristol-Myers Squibb (CJF). Its contents are solely the responsibility of the authors and do not necessarily represent the official views of the NIEHS, NIH, or BMS. We thank Dr. A. B. Dounay and Dr. G. Florence for critical reading of the manuscript.

Authors:  Craig J. Forsyth; Junliang Hao; Josep Aiguade
Journal:  Angew Chem Int Ed Engl       Date:  2001-10-01       Impact factor: 15.336

4.  Synthesis of the ABCD Ring System of Azaspiracid We thank Drs. D. H. Huang and G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. This work was financially supported by the National Institutes of Health (USA), The Skaggs Institute for Chemical Biology, a predoctoral fellowship from Bristol-Myers Squibb (to F.B.), postdoctoral fellowships from The Skaggs Institute for Research (to W.Q.), the Academy of Finland, the Ella and Georg Ehrnrooth Foundation and the Tauno Tönning Foundation (all to P.M.P.), and Bayer AG (to J.H.), as well as grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-La Roche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.

Authors:  K. C. Nicolaou; Wenyuan Qian; Federico Bernal; Noriaki Uesaka; Petri M. Pihko; Jürgen Hinrichs
Journal:  Angew Chem Int Ed Engl       Date:  2001-11-05       Impact factor: 15.336

5.  Synthesis of a 2,9-dioxabicyclo[3.3.1]nonane via double intramolecular hetero-Michael addition: entry to the F-G ring system of the azaspiracids.

Authors:  J Aiguade; J Hao; C J Forsyth
Journal:  Org Lett       Date:  2001-04-05       Impact factor: 6.005

6.  Synthetic studies toward the C5-C20 domain of the azaspiracids.

Authors:  A B Dounay; C J Forsyth
Journal:  Org Lett       Date:  2001-04-05       Impact factor: 6.005

7.  Two analogs of azaspiracid isolated from mussels, Mytilus edulis, involved in human intoxication in Ireland.

Authors:  K Ofuji; M Satake; T McMahon; J Silke; K J James; H Naoki; Y Oshima; T Yasumoto
Journal:  Nat Toxins       Date:  1999

8.  Studies directed toward the total synthesis of azaspiracid: stereoselective construction of C(1)-C(12), C(13)-C(19), and C(21)-C(25) fragments.

Authors:  R G Carter; D J Weldon
Journal:  Org Lett       Date:  2000-11-30       Impact factor: 6.005

9.  Structures of azaspiracid analogs, azaspiracid-4 and azaspiracid-5, causative toxins of azaspiracid poisoning in Europe.

Authors:  K Ofuji; M Satake; T Mcmahon; K J James; H Naoki; Y Oshima; T Yasumoto
Journal:  Biosci Biotechnol Biochem       Date:  2001-03       Impact factor: 2.043

10.  Synthesis of the ABC ring system of Azaspiracid. 2. A systematic study into the effect of C(16) and C(17) substitution on bis-spirocyclization.

Authors:  Rich G Carter; David E Graves; Melissa A Gronemeyer; Gregory S Tschumper
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005
  10 in total
  6 in total

1.  Synthesis of the ABCD and ABCDE ring systems of azaspiracid-1.

Authors:  Xiao-Ti Zhou; Rich G Carter
Journal:  Chem Commun (Camb)       Date:  2004-09-20       Impact factor: 6.222

2.  Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization.

Authors:  Xiao-Ti Zhou; Liang Lu; Daniel P Furkert; Charles E Wells; Rich G Carter
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

3.  Synthesis of the C1-C26 northern portion of azaspiracid-1: kinetic versus thermodynamic control of the formation of the bis-spiroketal.

Authors:  Xiao-Ti Zhou; Rich G Carter
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-03       Impact factor: 15.336

4.  Synthetic and Computational Studies on the ABC Trioxadispiroketal Subunit of the Marine Biotoxin Azaspiracid-1.

Authors:  Jialiang Li; Xiaohua Li; David R Mootoo
Journal:  Nat Prod Commun       Date:  2008-11       Impact factor: 0.986

5.  Synthesis of the ABC ring system of Azaspiracid. 2. A systematic study into the effect of C(16) and C(17) substitution on bis-spirocyclization.

Authors:  Rich G Carter; David E Graves; Melissa A Gronemeyer; Gregory S Tschumper
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

6.  Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis.

Authors:  David A Evans; Lisbet Kvaernø; Travis B Dunn; André Beauchemin; Brian Raymer; Jason A Mulder; Edward J Olhava; Martin Juhl; Katsuji Kagechika; David A Favor
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419
  6 in total

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