Premium
Single‐Step Construction of the anti ‐Deoxypropionate Motif from Propylene: Formal Total Synthesis of the Cuticular Hydrocarbons Isolated from Antitrogus parvulus
Author(s) -
Murayama Toshiki,
Nozaki Kyoko
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201804711
Subject(s) - motif (music) , stereochemistry , chemistry , single chain , structural motif , catalysis , organic chemistry , combinatorial chemistry , polymer chemistry , biology , biochemistry , physics , acoustics , antibody , immunology
Reported herein is the single‐step construction of an anti ‐configured deoxypropionate motif by syndiospecific propylene oligomerization catalyzed by a C s ‐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‐(2 R ,4 S ,6 R ,8 S )‐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.