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Literature DB >> 19281219

Enantioselective total synthesis of (-)-pironetin: iterative aldol reactions of thiazolidinethiones.

Michael T Crimmins¹, Anne-Marie R Dechert.

Abstract

The enantioselective total synthesis of pironetin has been achieved in 11 steps from known aldehyde 2. The synthesis relies on the formation of 5 out of 6 stereocenters through titanium mediated iterative aldol reactions. Key steps in this synthesis include an acetal aldol reaction to establish the stereochemistry at C8 and C9, an acetate aldol reaction, and "Evans" syn aldol reaction.

Entities: Chemical Disease Species

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Year: 2009 PMID： 19281219 PMCID： PMC2701212 DOI： 10.1021/ol9003228

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

23 in total

1. Catalytic asymmetric assembly of stereodefined propionate units: an enantioselective total synthesis of (-)-pironetin.

Authors: Xiaoqiang Shen; Andrew S Wasmuth; Junping Zhao; Cheng Zhu; Scott G Nelson
Journal: J Am Chem Soc Date: 2006-06-14 Impact factor: 15.419

2. Synthesis of a C(1)-C(14)-containing fragment of callipeltoside A.

Authors: T R Hoye; H Zhao
Journal: Org Lett Date: 1999-07-15 Impact factor: 6.005

3. Cell cycle arrest and antitumor activity of pironetin and its derivatives.

Authors: M Kondoh; T Usui; S Kobayashi; K Tsuchiya; K Nishikawa; T Nishikiori; T Mayumi; H Osada
Journal: Cancer Lett Date: 1998-04-10 Impact factor: 8.679

4. NK10958P, a novel plant growth regulator produced by Streptomyces sp.

Authors: K Tsuchiya; S Kobayashi; T Nishikiori; T Nakagawa; K Tatsuta
Journal: J Antibiot (Tokyo) Date: 1997-03 Impact factor: 2.649

5. Highly anti-selective asymmetric aldol reactions using chiral zirconium catalysts. Improvement of activities, structure of the novel zirconium complexes, and effect of a small amount of water for the preparation of the catalysts.

Authors: Yasuhiro Yamashita; Haruro Ishitani; Haruka Shimizu; Shū Kobayashi
Journal: J Am Chem Soc Date: 2002-04-03 Impact factor: 15.419

6. Total synthesis of the immunosupressant (-)-pironetin (PA48153C).

Authors: G E Keck; C E Knutson; S A Wiles
Journal: Org Lett Date: 2001-03-08 Impact factor: 6.005

7. Synthesis of (-)-stemoamide using a stereoselective anti-aldol step.

Authors: Horacio F Olivo; Ricardo Tovar-Miranda; Efraín Barragán
Journal: J Org Chem Date: 2006-04-14 Impact factor: 4.354

8. Magnesium halide-catalyzed anti-aldol reactions of chiral N-acylthiazolidinethiones.

Authors: David A Evans; C Wade Downey; Jared T Shaw; Jason S Tedrow
Journal: Org Lett Date: 2002-04-04 Impact factor: 6.005

9. A Mechanistic Study of the Horner-Wadsworth-Emmons Reaction: Computational Investigation on the Reaction Pass and the Stereochemistry in the Reaction of Lithium Enolate Derived from Trimethyl Phosphonoacetate with Acetaldehyde.

Authors: Kaori Ando
Journal: J Org Chem Date: 1999-09-03 Impact factor: 4.354

Enantioselective total synthesis of (-)-pironetin: iterative aldol reactions of thiazolidinethiones.

1. Catalytic asymmetric assembly of stereodefined propionate units: an enantioselective total synthesis of (-)-pironetin.

2. Synthesis of a C(1)-C(14)-containing fragment of callipeltoside A.

3. Cell cycle arrest and antitumor activity of pironetin and its derivatives.

4. NK10958P, a novel plant growth regulator produced by Streptomyces sp.

5. Highly anti-selective asymmetric aldol reactions using chiral zirconium catalysts. Improvement of activities, structure of the novel zirconium complexes, and effect of a small amount of water for the preparation of the catalysts.

6. Total synthesis of the immunosupressant (-)-pironetin (PA48153C).

7. Synthesis of (-)-stemoamide using a stereoselective anti-aldol step.

8. Magnesium halide-catalyzed anti-aldol reactions of chiral N-acylthiazolidinethiones.

9. A Mechanistic Study of the Horner-Wadsworth-Emmons Reaction: Computational Investigation on the Reaction Pass and the Stereochemistry in the Reaction of Lithium Enolate Derived from Trimethyl Phosphonoacetate with Acetaldehyde.

10. Titanium enolates of thiazolidinethione chiral auxiliaries: versatile tools for asymmetric aldol additions.

1. Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a.

2. 1-[(4S)-4-Benzyl-2-thioxo-1,3-thia-zol-idin-3-yl]propan-1-one.

Review 3. Bioinspired iterative synthesis of polyketides.

4. Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin.

5. The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid.

6. The taumycin A macrocycle: asymmetric total synthesis and revision of relative stereochemistry.