Synthesis of lignans. I. Nordihydroguaiaretc acid

CW Perry, MV Kalnins, KH Deitcher

文献索引：Perry,C.W. et al. Journal of Organic Chemistry, 1972 , vol. 37, # 26 p. 4371 - 4376

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被引用次数: 62

摘要

The novel alkylation of the sodium enolate of propioveratrone (4) with or- bromopropioveratrone (5) in liquid ammonia gave the racemic diketone 9. A mechanism for the stereoselectivity of this alkylation is proposed and the structural requirements of the reaction are discussed. Cyclodehydration of 9 to the furan 8 followed by hydrogenation via the all-cis tetrahydrofuran 25 afforded nordihydroguaiaretic acid (NDGA) tetramethyl ether ...