1. De Novo Asymmetric Synthesis of Phoracantholide J.
- Author
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Avocetien KF, Li JJ, Liu X, Wang Y, Xing Y, and O'Doherty GA
- Subjects
- Animals, Biological Products chemistry, Biological Products isolation & purification, Catalysis, Macrolides chemistry, Macrolides isolation & purification, Organometallic Compounds chemistry, Palladium chemistry, Ruthenium chemistry, Stereoisomerism, Biological Products chemical synthesis, Chemistry Techniques, Synthetic methods, Macrolides chemical synthesis
- Abstract
A de novo asymmetric total synthesis of the macrolide natural product (S)-phoracantholide J has been achieved in 10 steps from the commodity chemicals (1-pentyne, ethyl acrylate, acetaldehyde, and hydrogen). The asymmetry of the route was introduced by a Noyori reduction of a 3-yn-2-one, which makes the route equally amenable to the synthesis of either enantiomer. In addition, this route relies upon an alkyne zipper, a hydroalkynylation, and a macrolactonization to complete the synthesis.
- Published
- 2016
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