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CuCN-catalyzed reaction of the (1R)-isomer of 4-cyclopentene-1,3-diol monoacetate with TBDPSO(CH 2 ) 6 MgCl produced an S N 2-type product regioselectively in high yield. Mitsunobu inversion of the product and subsequent Claisen rearrangement furnished aldehyde with the two side chains, from which the title compounds were synthesized efficiently.
Among the three types of reagents from PhMgX (X=Br, Cl) and CuCN for phenylation of 4-cyclopentene-1,3-diol monoacetate, PhMgCl/CuCN (cat.) and Ph 2 Cu(CN)(MgCl) 2 in THF afforded the trans-1,4-isomer efficiently (82-87% yields, 91-93% regioselectivity). Similarly, o- and p-RC 6 H 4 MgCl (R=Me, OMe, CH 2 CH) in combination with CuCN furnished good to excellent...
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