Chiral secondary mixed alkylcopper-zinc reagents were prepared from the corresponding alkyl iodides and reacted with allylic epoxides via an anti-S_N2′-substitution and retention of configuration of the chiral alkylorganometallic, leading to chiral allylic alcohols. This method was used in a total synthesis of the natural product (3S,6R,7S)-zingiberenol in 8 steps and 9.7% overall yield [dr (3S,6R) = 99:1; dr (6R,7S) = 81:19] starting from commercially available 3-methyl-2-cyclohexenone.

中文翻译：

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立体选择性抗SN2'-取代烷基铜-锌试剂与烯丙基环氧化合物的合成：（3S，6R，7S）-姜黄烯醇的全合成

由相应的烷基碘制备手性仲烷基铜-锌混合试剂，并通过抗-S _N 2'取代与烯丙基环氧化物反应，并保留手性烷基有机金属的构型，从而形成手性烯丙基醇。该方法用于8个步骤的天然产物（3 S，6 R，7 S）-姜黄烯醇的全合成中，总收率[dr（3 S，6 R）= 99：1; Dr（6 R，7 S）= 81:19]从市售的3-甲基-2-环己烯酮开始。