1-Nitro-1-(phenylthio) propene as a new nitro olefin reagent for 3-methylfuran annulation and its application to the synthesis of some furanoterpenoids

…, T Kumazawa, A Yoshikoshi

文献索引：Miyashita, Masaaki; Kumazawa, Toshiaki; Yoshikoshi, Akira Journal of Organic Chemistry, 1980 , vol. 45, # 15 p. 2945 - 2950

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被引用次数: 70

摘要

1-Nitro-1-(pheny1thio) propene (9) was synthesized from (pheny1thio) acetic acid (6) in five steps. This nitro olefin reacted with dimedone (1) with KF catalysis to yield dihydrofurans loa and lob, both of which were converted to 3-methylfuran 13 on NdO4 oxidation followed by elimination of benzenesulfenic acid from the resulting sulfoxides in good overall yields. As an application of this reagent, the furanomonoterpenoid evodone (24) and the ...