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Charge neutral TpMo(CO)(2)(5-acyloxy-eta(3)-pyranyl) and TpMo(CO)(2)(5-acyloxy-eta(3)-pyridinyl) scaffolds undergo a novel intermolecular "homo-S(N)2'-like" reaction with a variety of carbon nucleophiles. Combined with an annulative demetalation, the homo-S(N)2'-like substitution/annulative demetalation sequence rapidly generates 2,7-dioxabicyclo[4.3.0]nonane and 2-aza-7-oxabicyclo[4.3.0]nonane frameworks in good to excellent yields with high enantiopurity. An enantiocontrolled total synthesis of the antimalarial alkaloid (+)-isofebrifugine was achieved utilizing this reaction cascade.

journal of the american chemical society

A New Reaction Motif: “Homo-S<sub>N</sub>2′-Like” Direct Nucleophilic Addition to Neutral η<sup>3</sup>-Allylmolybdenum Complexes. Total Synthesis of the Antimalarial (+)-Isofebrifugine

A New Reaction Motif: “Homo-SN2′-Like” Direct Nucleophilic Addition to Neutral η3-Allylmolybdenum Complexes. Total Synthesis of the Antimalarial (+)-Isofebrifugine

A New Reaction Motif: “Homo-S_N2′-Like” Direct Nucleophilic Addition to Neutral η³-Allylmolybdenum Complexes. Total Synthesis of the Antimalarial (+)-Isofebrifugine