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Literature DB >> 15467841

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

Abstract

The efficient syntheses of the ABCD ring system of the originally proposed structure of azaspiracid-1 and the ABCDE ring system of the revised structure of azaspiracid-1 containing the correct stereochemistry at C(6), C(10), C(13), C(14), C(16), C(17), C(19), C(21), C(22), C(24) and C(25) have been achieved.

Entities: Chemical Disease

Mesh：

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Year: 2004 PMID： 15467841 PMCID： PMC2427370 DOI： 10.1039/b410092a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

19 in total

1. 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

2. 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

3. 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

4. Total synthesis of the proposed azaspiracid-1 structure, part 1: construction of the enantiomerically pure C1-C20, C21-C27, and C28-C40 fragments.

Authors: K C Nicolaou; Yiwei Li; Noriaki Uesaka; Theocharis V Koftis; Stepan Vyskocil; Taotao Ling; Mugesh Govindasamy; Wenyuan Qian; Federico Bernal; David Y-K Chen
Journal: Angew Chem Int Ed Engl Date: 2003-08-11 Impact factor: 15.336

5. Total synthesis of the proposed azaspiracid-1 structure, part 2: coupling of the C1-C20, C21-C27, and C28-C40 fragments and completion of the synthesis.

Authors: K C Nicolaou; David Y-K Chen; Yiwei Li; Wenyuan Qian; Taotao Ling; Stepan Vyskocil; Theocharis V Koftis; Mugesh Govindasamy; Noriaki Uesaka
Journal: Angew Chem Int Ed Engl Date: 2003-08-11 Impact factor: 15.336

6. 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

7. A dirhodium(II)-carbenoid route to (-)- and (+)-Geissman-Waiss lactone: synthesis of (1R,7R,8R)-(-)-turneforcidine.

Authors: A G Wee
Journal: J Org Chem Date: 2001-12-14 Impact factor: 4.354

8. Total synthesis of fostriecin (CI-920).

Authors: D L Boger; S Ichikawa; W Zhong
Journal: J Am Chem Soc Date: 2001-05-09 Impact factor: 15.419

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

Authors: Rich G Carter; T Campbell Bourland; David E Graves
Journal: Org Lett Date: 2002-06-27 Impact factor: 6.005

10. First evidence of an extensive northern European distribution of azaspiracid poisoning (AZP) toxins in shellfish.

Authors: Kevin J James; Ambrose Furey; Mary Lehane; Hanne Ramstad; Tore Aune; Peter Hovgaard; Steven Morris; Wendy Higman; Masayuki Satake; Takeshi Yasumoto
Journal: Toxicon Date: 2002-07 Impact factor: 3.033

6 in total

1. 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

2. 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