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Total Synthesis of (−)‐Acetylaranotin
Author(s) -
Fujiwara Hideto,
Kurogi Taichi,
Okaya Shun,
Okano Kentaro,
Tokuyama Hidetoshi
Publication year - 2012
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.201207307
Subject(s) - regioselectivity , total synthesis , ring (chemistry) , chemistry , stereochemistry , organic chemistry , combinatorial chemistry , catalysis
The key step in this total synthesis of (−)‐acetylaranotin is the efficient formation of the characteristic dihydrooxepine ring from cyclohexenone through an unusual vinylogous Rubottom oxidation and a regioselective Baeyer–Villiger oxidation. (−)‐Acetylaranotin is obtained in 22 steps from commercially available L ‐Cbz‐tyrosine (Cbz=benzyloxycarbonyl).