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Literature DB >> 12074662

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.

Rich G Carter¹, David E Graves, Melissa A Gronemeyer, Gregory S Tschumper.

Abstract

[reaction: see text] A systematic study into the effect of C(16) and C(17) substitution on the stereochemical outcome of bis-spirocyclization to form the ABC ring system of azaspiracid is disclosed. Successful construction of the natural 10R,13R bis-spirocyclic stereochemistry has been accomplished on the C(16) benzyloxy-containing precursor.

Entities: Chemical Gene

Mesh：

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Year: 2002 PMID： 12074662 PMCID： PMC2424254 DOI： 10.1021/ol026034o

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

6 in total

1. 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

2. A by-product using TIPS protection--a warning.

Authors: D J Barden; I Fleming
Journal: Chem Commun (Camb) Date: 2001-11-21 Impact factor: 6.222

3. 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

4. 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

5. 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

6. 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

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