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Literature DB >> 15151414

Trans-selective conversions of gamma-hydroxy-alpha,beta-alkynoic esters to gamma-hydroxy-alpha,beta-alkenoic esters.

Abstract

Gamma-hydroxy-alpha,beta-acetylenic esters are used as precursors to prepare gamma-hydroxy-alpha,beta-alkenoic esters by means of trans-selective additions of two hydrogen atoms or one hydrogen atom and one iodine atom across the triple bonds. These methods allow for the preparation of beta-substituted and alpha,beta-disubstituted alkenoic esters in highly stereoselective manners. [reaction--see text]

Entities: Chemical

Year: 2004 PMID： 15151414 DOI： 10.1021/ol0495366

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

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Cited

11 in total

1. Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue.

Authors: Brian J Albert; Ananthapadmanabhan Sivaramakrishnan; Tadaatsu Naka; Nancy L Czaicki; Kazunori Koide
Journal: J Am Chem Soc Date: 2007-02-06 Impact factor: 15.419

2. The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

Authors: Barry M Trost; Andrew H Weiss
Journal: Adv Synth Catal Date: 2009-05 Impact factor: 5.837

3. Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids.

Authors: Amaresh R Rajaram; Lin Pu
Journal: Org Lett Date: 2006-05-11 Impact factor: 6.005

4. Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

Authors: Barry M Trost; Mark J Bartlett; Andrew H Weiss; Axel Jacobi von Wangelin; Vincent S Chan
Journal: Chemistry Date: 2012-10-23 Impact factor: 5.236

5. Cyclic Acetal Formation Between 2-Pyridinecarboxaldehyde and gamma-Hydroxy-alpha,beta-Acetylenic Esters.

Authors: Sami Osman; Kazunori Koide
Journal: Tetrahedron Lett Date: 2008-11-10 Impact factor: 2.415

6. Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride.

Authors: Subrata Kumar Chaudhuri; Manabendra Saha; Amit Saha; Sanjay Bhar
Journal: Beilstein J Org Chem Date: 2010-09-02 Impact factor: 2.883

Trans-selective conversions of gamma-hydroxy-alpha,beta-alkynoic esters to gamma-hydroxy-alpha,beta-alkenoic esters.

1. Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue.

2. The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

3. Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids.

4. Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

5. Cyclic Acetal Formation Between 2-Pyridinecarboxaldehyde and gamma-Hydroxy-alpha,beta-Acetylenic Esters.

6. Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride.

Review 7. Spliceostatins and Derivatives: Chemical Syntheses and Biological Properties of Potent Splicing Inhibitors.

8. trans-Hydrogenation: application to a concise and scalable synthesis of brefeldin A.

9. trans-Hydrogenation: Application to a Concise and Scalable Synthesis of Brefeldin A.

10. Guiding a divergent reaction by photochemical control: bichromatic selective access to levulinates and butenolides.