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. 2018 Aug 27;57(35):11394-11398.
doi: 10.1002/anie.201804711. Epub 2018 Jul 26.

Single-Step Construction of the anti-Deoxypropionate Motif from Propylene: Formal Total Synthesis of the Cuticular Hydrocarbons Isolated from Antitrogus parvulus

Toshiki Murayama  1 , Kyoko Nozaki  1
Affiliations

Single-Step Construction of the anti-Deoxypropionate Motif from Propylene: Formal Total Synthesis of the Cuticular Hydrocarbons Isolated from Antitrogus parvulus

Toshiki Murayama et al. Angew Chem Int Ed Engl. .

Abstract

Reported herein is the single-step construction of an anti-configured deoxypropionate motif by syndiospecific propylene oligomerization catalyzed by a Cs -symmetric zirconocene complex. After oligomerization, oxidation of the oligomers by oxygen afforded oligopropylene alcohols in a single step. This strategy was applied to the single-step preparation of rel-(2R,4S,6R,8S)-2,4,6,8-tetramethylundecan-1-ol, the racemic mixture of the synthetic fragment of the cuticular hydrocarbons isolated from the cane beetle Antitrogus parvulus.

Keywords: diastereomers; natural products; oligomerization; zinc; zirconium.

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