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
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- PMID: 29953709
- DOI: 10.1002/anie.201804711
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Single-Step Construction of the anti-Deoxypropionate Motif from Propylene: Formal Total Synthesis of the Cuticular Hydrocarbons Isolated from Antitrogus parvulus
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.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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