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Synthesis of a 10‐Membered Carbocycle By Olefin Metathesis
Author(s) -
Nevalainen Marta,
Koskinen Ari M. P.
Publication year - 2001
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 - 10.1002/1521-3773(20011105)40:21<4060::aid-anie4060>3.0.co;2-8
Subject(s) - olefin metathesis , metathesis , ether , sesquiterpene , olefin fiber , ring (chemistry) , chemistry , stereochemistry , organic chemistry , catalysis , polymerization , polymer
Even 10‐membered rings can be obtained by ring‐closing metathesis (RCM). The synthesis of carbocycle B by RCM, which is the key step in the synthesis of the pine‐resin sesquiterpene 1,6‐germacradien‐5‐ol, was improved by protecting the hydroxy group of the precursor bisolefin A as a bulky tert ‐butyldimethylsilyl ether and by complexing its carbonyl group with Ti(O i Pr) 4 .