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Literature DB >> 27685496

Asymmetric Synthesis of Homocitric Acid Lactone.

Leslie A Nickerson¹, Valerie Huynh¹, Edward I Balmond¹, Stephen P Cramer¹, Jared T Shaw¹.

Abstract

A short, diastereoselective synthesis of homocitric acid lactone is described. The key step is a bioinspired aldol addition to set the stereogenic center in an intermediate that requires only modest oxidation state manipulation to complete the synthesis. This approach enables rapid generation of isotopomers in which carbon and hydrogen can be replaced by heavier nuclei at nearly every position.

Entities: Chemical Species

Mesh：

Substances：

Year: 2016 PMID： 27685496 PMCID： PMC7190193 DOI： 10.1021/acs.joc.6b01997

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

18 in total

1. Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes.

Authors: Nathan R Guz; Andrew J Phillips
Journal: Org Lett Date: 2002-06-27 Impact factor: 6.005

2. Homocitrate is a component of the iron-molybdenum cofactor of nitrogenase.

Authors: T R Hoover; J Imperial; P W Ludden; V K Shah
Journal: Biochemistry Date: 1989-04-04 Impact factor: 3.162

3. Highly selective acetate aldol additions using mesityl-substituted chiral auxiliaries.

Authors: Michael T Crimmins; Mariam Shamszad
Journal: Org Lett Date: 2007-01-04 Impact factor: 6.005

4. Synthesis of a new N-acetyl thiazolidinethione reagent and its application to a highly selective asymmetric acetate aldol reaction.

Authors: Yingchao Zhang; Tarek Sammakia
Journal: Org Lett Date: 2004-09-02 Impact factor: 6.005

5. Indene-based thiazolidinethione chiral auxiliary for propionate and acetate aldol additions.

Authors: Antonio Osorio-Lozada; Horacio F Olivo
Journal: Org Lett Date: 2008-01-19 Impact factor: 6.005

6. Structural models for the metal centers in the nitrogenase molybdenum-iron protein.

Authors: J Kim; D C Rees
Journal: Science Date: 1992-09-18 Impact factor: 47.728

7. Total Synthesis of Biselyngbyolide B.

Authors: Eisuke Sato; Yurika Tanabe; Naoya Nakajima; Akifumi Ohkubo; Kiyotake Suenaga
Journal: Org Lett Date: 2016-04-11 Impact factor: 6.005

8. The selective inhibition of phosphatases by natural toxins: the anhydride domain of tautomycin is not a primary factor in controlling PP1/PP2A selectivity.

Authors: Wen Liu; James E Sheppeck; David A Colby; Hsien-Bin Huang; Angus C Nairn; A Richard Chamberlin
Journal: Bioorg Med Chem Lett Date: 2003-05-05 Impact factor: 2.823

Asymmetric Synthesis of Homocitric Acid Lactone.

1. Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes.

2. Homocitrate is a component of the iron-molybdenum cofactor of nitrogenase.

3. Highly selective acetate aldol additions using mesityl-substituted chiral auxiliaries.

4. Synthesis of a new N-acetyl thiazolidinethione reagent and its application to a highly selective asymmetric acetate aldol reaction.

5. Indene-based thiazolidinethione chiral auxiliary for propionate and acetate aldol additions.

6. Structural models for the metal centers in the nitrogenase molybdenum-iron protein.

7. Total Synthesis of Biselyngbyolide B.

8. The selective inhibition of phosphatases by natural toxins: the anhydride domain of tautomycin is not a primary factor in controlling PP1/PP2A selectivity.

9. Total syntheses of amphidinolides B1, B4, G1, H1 and structure revision of amphidinolide H2.

10. Enantioselective synthesis of isotopically labeled homocitric acid lactone.

1. Direct Access to Highly Functionalized Heterocycles through the Condensation of Cyclic Imines and α-Oxoesters.

2. A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters.