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Literature DB >> 16470899

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

Xiao-Ti Zhou¹, Rich G Carter.

Abstract

Entities: Chemical

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Year: 2006 PMID： 16470899 PMCID： PMC2414258 DOI： 10.1002/anie.200503733

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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17 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. 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

3. 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

4. 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

5. 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

6. 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

7. 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

8. A stereoselective and short total synthesis of the polyhydroxylated gamma-amino acid (-)-detoxinine, based on stereoselective preparation of dihydropyrrole derivatives from lithiated alkoxyallenes.

Authors: Oliver Flögel; Marlyse Ghislaine Okala Amombo; Hans-Ulrich Reissig; Gernot Zahn; Irene Brüdgam; Hans Hartl
Journal: Chemistry Date: 2003-03-17 Impact factor: 5.236

9. 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. 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

11 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. Enantioselective total synthesis of lycopodine.

Authors: Hua Yang; Rich G Carter; Lev N Zakharov
Journal: J Am Chem Soc Date: 2008-06-27 Impact factor: 15.419

3. An iodoetherification-dehydroiodination strategy for the synthesis of complex spiroketals from dihydroxyalkene precursors.

Authors: K A Tony; Xiaohua Li; Darrin Dabideen; Jialiang Li; David R Mootoo
Journal: Org Biomol Chem Date: 2008-02-22 Impact factor: 3.876

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

3. 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.

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

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

6. 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.

7. 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.

8. A stereoselective and short total synthesis of the polyhydroxylated gamma-amino acid (-)-detoxinine, based on stereoselective preparation of dihydropyrrole derivatives from lithiated alkoxyallenes.

9. 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.

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

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

2. Enantioselective total synthesis of lycopodine.

3. An iodoetherification-dehydroiodination strategy for the synthesis of complex spiroketals from dihydroxyalkene precursors.

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

5. Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

6. Development of an enantioselective route toward the Lycopodium alkaloids: total synthesis of lycopodine.

7. Enantioselective total synthesis of amphidinolide F.

8. Efficient synthesis of the C(7)-C(20) subunit of amphidinolides C and F.

9. Olefin metathesis-iodoetherification-dehydroiodination strategy for spiroketal subunits of polyether antibiotics.

10. Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F.