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Literature DB >> 11671381

Diastereoselective Synthesis of an Isoprostane: (+/-)-8-epi-PGF(2)(alpha) Ethyl Ester.

Douglass F. Taber¹, R. Jason Herr, D. Mark Gleave.

Abstract

A total synthesis of the isoprostane (+/-)-8-epi-PGF(2)(alpha) ethyl ester (5) is described, based on the diastereoselective cyclization of alpha-diazo ketone 7. This ketone is assembled by aldol condensation between alpha-diazo ketone 8 and aldehyde 9. The sequential alpha-diazo ketone aldol/insertion described here offers a powerful new approach to cycloalkane construction.

Entities: Chemical Gene

Year: 1997 PMID： 11671381 DOI： 10.1021/jo9616365

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

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Cited

5 in total

1. Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles.

Authors: Jeffrey S Cannon; Angela C Olson; Larry E Overman; Nicole S Solomon
Journal: J Org Chem Date: 2012-02-08 Impact factor: 4.354

2. A new approach to the synthesis of polyunsaturated deuterated isoprostanes: total synthesis of d4-5-epi-8,12-iso-iPF3alpha-VI and d4-8,12-iso-iPF3alpha-VI.

Authors: Chih-Tsung Chang; Pranav Patel; Vivek Gore; Wen-Liang Song; John A Lawson; William S Powell; Garret A Fitzgerald; Joshua Rokach
Journal: Bioorg Med Chem Lett Date: 2009-09-29 Impact factor: 2.823

Diastereoselective Synthesis of an Isoprostane: (+/-)-8-epi-PGF(2)(alpha) Ethyl Ester.

1. Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles.

2. A new approach to the synthesis of polyunsaturated deuterated isoprostanes: total synthesis of d4-5-epi-8,12-iso-iPF3alpha-VI and d4-8,12-iso-iPF3alpha-VI.

3. Preparation of the Major Urinary Metabolite of (-)-Prostaglandin E(2).

4. Oxidative stress, obesity, and breast cancer risk: results from the Shanghai Women's Health Study.

5. A Study to Validate the Relevance of Semen F₂-Isoprostanes on Human Male Infertility.

Diastereoselective Synthesis of an Isoprostane: (+/-)-8-epi-PGF(2)(alpha) Ethyl Ester.

1. Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles.

2. A new approach to the synthesis of polyunsaturated deuterated isoprostanes: total synthesis of d4-5-epi-8,12-iso-iPF3alpha-VI and d4-8,12-iso-iPF3alpha-VI.

3. Preparation of the Major Urinary Metabolite of (-)-Prostaglandin E(2).

4. Oxidative stress, obesity, and breast cancer risk: results from the Shanghai Women's Health Study.

5. A Study to Validate the Relevance of Semen F2-Isoprostanes on Human Male Infertility.

5. A Study to Validate the Relevance of Semen F₂-Isoprostanes on Human Male Infertility.