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Anion-catalyzed addition of gamma-silylallenyl esters to aldehydes: a new entry into [3.2.1] bicyclic natural products.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2009 Apr 01; Vol. 131 (12), pp. 4196-7. - Publication Year :
- 2009
-
Abstract
- A significant improvement in the generality and reactivity of MBH-type reactions is made possible by anion catalysis and a 1,3-Brook rearrangement. In this new reaction, both aliphatic and aromatic aldehydes are rapidly added to silylallenes, leading to gamma-carbinol allenoates at low temperatures. The utility of these reaction products is demonstrated by a fast-tracked synthesis of a [3.2.1] bisoxa bicycle that makes up the framework of many biologically active natural products, including vitisinol D, an antithrombotic agent.
- Subjects :
- Anions
Biflavonoids chemistry
Bridged Bicyclo Compounds chemistry
Catalysis
Catechin chemical synthesis
Catechin chemistry
Chemistry, Organic methods
Chemistry, Pharmaceutical methods
Drug Design
Models, Chemical
Molecular Structure
Proanthocyanidins chemistry
Substrate Specificity
Temperature
Aldehydes chemistry
Bridged Bicyclo Compounds chemical synthesis
Catechin analogs & derivatives
Esters chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 131
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 19271702
- Full Text :
- https://doi.org/10.1021/ja810136m