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Literature DB >> 19634891

Stereoselective synthesis of benzannulated spiroketals: influence of the aromatic ring on reactivity and conformation.

Guodong Liu¹, Jacqueline M Wurst, Derek S Tan.

Abstract

A systematic stereocontrolled synthesis of benzannulated spiroketals has been developed, using kinetic spirocyclization reactions of glycal epoxides, leading to a new AcOH-induced cyclization and valuable insights into the reactivity and conformations of these systems. One stereochemical series accommodates axial positioning of the aromatic ring while another adopts an alternative (1)C(4) chair conformation to avoid it. Equatorial aromatic rings also participate in nonobvious steric interactions that impact thermodynamic stability. A discovery library of 68 benzannulated spiroketals with systematic variations in stereochemistry, ring size, and positioning of the aromatic substituent has been synthesized for broad biological evaluation.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2009 PMID： 19634891 PMCID： PMC2760470 DOI： 10.1021/ol901437f

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

19 in total

1. The Total Synthesis of Heliquinomycinone This work was supported by the National Institutes of Health (Grant numbers: AI 16943 and HL25848). The authors thank Dr. Makoto Chino of Nippon Kayaku Co., Ltd. for kindly providing a sample of heliquinomycin, and Yashuiro Itagaki of Columbia University for high-resolution mass spectral analyses.

Authors: Tony Siu; Donghui Qin; Samuel J. Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2001-12-17 Impact factor: 15.336

2. Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile.

Authors: Andrea A Stierle; Donald B Stierle; Kal Kelly
Journal: J Org Chem Date: 2006-07-07 Impact factor: 4.354

3. Total synthesis of papulacandin D.

Authors: Scott E Denmark; Christopher S Regens; Tetsuya Kobayashi
Journal: J Am Chem Soc Date: 2007-02-17 Impact factor: 15.419

4. Total synthesis of (+/-)-gamma-rubromycin on the basis of two aromatic Pummerer-type reactions.

Authors: Shuji Akai; Keisuke Kakiguchi; Yuka Nakamura; Ikumi Kuriwaki; Toshifumi Dohi; Shusaku Harada; Ozora Kubo; Nobuyoshi Morita; Yasuyuki Kita
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. Stereocontrolled synthesis of spiroketals via a remarkable methanol-induced kinetic spirocyclization reaction.

Authors: Justin S Potuzak; Sirkka B Moilanen; Derek S Tan
Journal: J Am Chem Soc Date: 2005-10-12 Impact factor: 15.419

6. Enantioselective synthesis of erythro-4-deoxyglycals as scaffolds for target- and diversity-oriented synthesis: new insights into glycal reactivity.

Authors: Sirkka B Moilanen; Derek S Tan
Journal: Org Biomol Chem Date: 2005-01-24 Impact factor: 3.876

7. Epoxide-opening cascades promoted by water.

Authors: Ivan Vilotijevic; Timothy F Jamison
Journal: Science Date: 2007-08-31 Impact factor: 47.728

8. Direct kinetic formation of nonanomeric [6.5]-spiroketals in aqueous media.

Authors: Daniele Castagnolo; Irene Breuer; Petri M Pihko
Journal: J Org Chem Date: 2007-11-16 Impact factor: 4.354

9. Diastereoselective syntheses of chroman spiroketals via [4 + 2] cycloaddition of enol ethers and o-quinone methides.

Authors: Maurice A Marsini; Yaodong Huang; Christopher C Lindsey; Kun-Liang Wu; Thomas R R Pettus
Journal: Org Lett Date: 2008-03-13 Impact factor: 6.005

10. Facile synthesis of naphthoquinone spiroketals by diastereoselective oxidative [3 + 2] cycloaddition.

Authors: Kun-Liang Wu; Stephanie Wilkinson; Norbert O Reich; Thomas R R Pettus
Journal: Org Lett Date: 2007-11-29 Impact factor: 6.005

12 in total

Review 1. Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors: Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal: J Comb Chem Date: 2010-10-05

2. Total Synthesis of (+)-Papulacandin D.

Authors: Scott E Denmark; Tetsuya Kobayashi; Christopher S Regens
Journal: Tetrahedron Date: 2010-06-26 Impact factor: 2.457

3. Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals.

Authors: Jacqueline M Wurst; Guodong Liu; Derek S Tan
Journal: J Am Chem Soc Date: 2011-05-03 Impact factor: 15.419

Stereoselective synthesis of benzannulated spiroketals: influence of the aromatic ring on reactivity and conformation.

2. Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile.

3. Total synthesis of papulacandin D.

4. Total synthesis of (+/-)-gamma-rubromycin on the basis of two aromatic Pummerer-type reactions.

5. Stereocontrolled synthesis of spiroketals via a remarkable methanol-induced kinetic spirocyclization reaction.

6. Enantioselective synthesis of erythro-4-deoxyglycals as scaffolds for target- and diversity-oriented synthesis: new insights into glycal reactivity.

7. Epoxide-opening cascades promoted by water.

8. Direct kinetic formation of nonanomeric [6.5]-spiroketals in aqueous media.

9. Diastereoselective syntheses of chroman spiroketals via [4 + 2] cycloaddition of enol ethers and o-quinone methides.

10. Facile synthesis of naphthoquinone spiroketals by diastereoselective oxidative [3 + 2] cycloaddition.

Review 1. Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

2. Total Synthesis of (+)-Papulacandin D.

3. Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals.

4. Stereoselective synthesis of acortatarins A and B.

5. A divergent enantioselective strategy for the synthesis of griseusins.

6. Stereocontrolled Synthesis of Spiroketals: An Engine for Chemical and Biological Discovery.

7. Synthesis and antifungal properties of papulacandin derivatives.

8. Turning Spiroketals Inside Out: A Rearrangement Triggered by an Enol Ether Epoxidation.

9. Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups.

10. Solvent-dependent divergent functions of Sc(OTf)₃ in stereoselective epoxide-opening spiroketalizations.