AI Article Synopsis
- Researchers created complex medium-sized cyclic ethers similar to those in natural products using a series of chemical reactions, including ring-closing metathesis and Tsuji-Trost allylation.
- They converted the initial compounds into specific types of enol carbonates for further reactions, which allowed for better control over the final product's structure.
- The study achieved high diastereocontrol, favoring a specific molecular configuration when the catalyst used matched the design of the starting material.
Article Abstract
Fully functionalized medium-sized cyclic ethers, of the type found in fused polyether natural products, have been prepared by sequential ring-closing diene metathesis, conversion of the resulting cyclic enone into an allylic enol carbonate, and Tsuji-Trost allylation using a chiral palladium complex. Very high levels of diastereocontrol, favoring the diastereomer in which there is a cis relationship between the allyl group at C-2 of the medium-ring ether and the substituent at C-7/C-8, are obtained in cases where catalyst control and substrate control are matched.
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| http://dx.doi.org/10.1021/acs.orglett.8b01082 | DOI Listing |
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