1. De Novo Asymmetric Synthesis of Phoracantholide J
- Author
-
Xiaofan Liu, Yalan Xing, Yanping Wang, Kenneth F. Avocetien, George A. O'Doherty, and Jiazhen J. Li
- Subjects
Stereochemistry ,Alkyne ,Stereoisomerism ,Chemistry Techniques, Synthetic ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Catalysis ,Ruthenium ,chemistry.chemical_compound ,Organometallic Compounds ,Animals ,Physical and Theoretical Chemistry ,chemistry.chemical_classification ,Biological Products ,Natural product ,010405 organic chemistry ,Organic Chemistry ,Enantioselective synthesis ,Acetaldehyde ,Total synthesis ,0104 chemical sciences ,chemistry ,Ethyl acrylate ,Macrolides ,Enantiomer ,Palladium - 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