Retrosynthetic analysis of (3S,6R,7S)-zingiberenol

August 13, 2024

• Title:       

  Retrosynthetic analysis of (3S,6R,7S)-zingiberenol

• Image Source:

  Stereoselective anti-S_N2′-Substitutions of Secondary Alkylcopper-Zinc Reagents with Allylic Epoxides: Total Synthesis of (3S, 6R, 7S)-Zingiberenol

• Mark:

  Figure 1

• Associated context:

  An example of a chiral cyclic allylic alcohol is the natural product zingiberenol (8) (see Figure 1).6 Only two of  8 possible stereoisomers exist in nature, (3S,6R,7S)- and  (3S,6S,7S)-zingiberenol. Retrosynthetic analysis showed that (3S,6R,7S)-zingiberenol (8) can be prepared via an anti-SN2′-substitution reaction of the chiral allylic epoxide 9 and the copper reagent 10 (prepared from the corresponding al-kyliodide11, see Figure 1).