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- W2172029247 abstract "Following the strategy of Scheme 1, a Mukaiyama aldol addition/anti-elimination route to stereopure γ-alkylidenebutenolides 4 was established. The addition giving 27 was only moderately diastereoselective but the products lk- and ul-27 were chromatographically separable (Scheme 4). They underwent highly selective anti-eliminations in the presence of triflic anhydride–pyridine or Burgess' reagent, furnishing the thiophene-containing butenolides Z- and E-28, respectively (Scheme 5). The Mukaiyama aldol addition leading to compound 29 was 100% lk-selective when mediated by BF3 etherate and 87:13 ul-selective in the presence of ZnBr2 (Scheme 6). Stephens–Castro couplings of the resulting butenolides lk- and ul-29 with 3-ethynylfuran proceeded with complete conservation of the stereochemical integrity (Scheme 7). The subsequent anti-eliminations of water were best realized by treatment with DEAD–PPh3. They provided freelingyne (Z-9) with ds=92:8 and its isomer E-9 with ds=98: 2 (Scheme 8). Analogously, the differently substituted (trimethylsiloxy)furans 15 or 16 provided the freelingyne analogs Z-10, E-10 and Z-11 (Schemes 6–8)." @default.
- W2172029247 created "2016-06-24" @default.
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- W2172029247 date "2000-01-01" @default.
- W2172029247 modified "2023-10-09" @default.
- W2172029247 title "Stereoselective synthesis of freelingyne and related γ-alkylidenebutenolides via vinylogous Mukaiyama aldol additions" @default.
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- W2172029247 doi "https://doi.org/10.1039/b002903n" @default.
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