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.
Highlights
Medium-sized cyclic ethers occur frequently as subunits in marine natural products
Asymmetric Tsuji−Trost Allylation Reaction Applied to Polyether Fragment Coupling contain an abundance of both saturated and unsaturated medium-sized cyclic ethers ranging in size from seven to nine.[1]
The seven-membered cyclic ether substrates required for the Tsuji−Trost allylation reaction were prepared as shown in Scheme 3
Summary
Medium-sized cyclic ethers occur frequently as subunits in marine natural products. Fused polycyclic ether natural products such as CTX-3C (1) (Figure 1) have structures that highly functionalized medium-sized cyclic ethers and applying them to the efficient preparation of fused polycyclic ether frameworks by iterative ring construction.[4]. The seven-membered cyclic ether substrates required for the Tsuji−Trost allylation reaction were prepared as shown in Scheme 3.
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