An Efficient Total Synthesis of (-)-(R), (+)-(S)-Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric alpha-Aminooxylation and [3,3] Claisen Rearrangement

作者：Bhosale Viraj A^*; Waghmode Suresh B^*

来源：ChemistrySelect, 2017, 2(3): 1262-1266.

DOI：10.1002/slct.201601890

• Aminooxylation
• Claisen rearrangement
• Grignard Reaction
• Stereodivergent
• Wittig reaction

An efficient total synthesis of the enantiomerically pure lavandulol pheromones viz. (-)-(R) and (+)-(S)-lavandulol, (-)-(R)-lavandulyl acetate, (-)-(R)-lavandulyl propionate, (+)-(S)lavandulyl 2-methylbutanoate and (+)-(S)-lavandulyl senecioate is accomplished from nonchiral and chiral materials. The strategy utilizes a sequence of proline catalyzed asymmetric alpha-aminooxylation and [3,3] Claisen rearrangement for stereodivergent synthesis of chiral C-2 unit containing 4-pentenols.

• 出版日期2017-1