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Skotnitzki, Juri; Kremsmair, Alexander; Kicin, Bilal; Saeb, Rakan; Ruf, Vincent and Knochel, Paul (2020): Stereoselective anti-S(N)2 '-Substitutions of Secondary Alkylcopper-Zinc Reagents with Allylic Epoxides: Total Synthesis of (3S,6R,7S)-Zingiberenol. In: Synthesis-Stuttgart, Vol. 52, No. 6: pp. 873-881

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Chiral secondary mixed alkylcopper-zinc reagents were prepared from the corresponding alkyl iodides and reacted with allylic epoxides via an anti -S (N) 2 '-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 (3 S ,6 R ,7 S )-zingiberenol in 8 steps and 9.7% overall yield [dr (3 S ,6 R ) = 99:1;dr (6 R ,7 S ) = 81:19] starting from commercially available 3-methyl-2-cyclohexenone.

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