AI Article Synopsis
- Xyloketal B is a natural compound from marine fungi with potential therapeutic applications for diseases like Alzheimer's and atherosclerosis.
- The first asymmetric synthesis of Xyloketal B was achieved using a chemoenzymatic method that involves a biocatalytic process and [4 + 2] cycloaddition to create a crucial cyclic ketal intermediate.
- The synthesis was completed by generating another quinone methide through a reductive method, successfully producing stereoselective (+)-xyloketal B, with its structure confirmed using MicroED technology.
Article Abstract
Xyloketal B is a pentacyclic fungal marine natural product that has shown potential for the treatment of diseases such as Alzheimer's disease and atherosclerosis. Herein, we describe the first asymmetric synthesis of this natural product, which relies on a chemoenzymatic strategy. This approach leverages a biocatalytic benzylic hydroxylation to access to an quinone methide intermediate which is captured in a [4 + 2] cycloaddition to stereoselectively yield a key cyclic ketal intermediate enroute to (+)-xyloketal B. The relative configuration of this intermediate was rapidly confirmed as the desired stereoisomer using MicroED. To complete the synthesis, a second -quinone methide was accessed through a reductive approach, ultimately leading to the stereoselective synthesis of (+)-xyloketal B.
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