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Total synthesis of (-)-acetylaranotin.

Authors :
Fujiwara H
Kurogi T
Okaya S
Okano K
Tokuyama H
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2012 Dec 21; Vol. 51 (52), pp. 13062-5. Date of Electronic Publication: 2012 Nov 19.
Publication Year :
2012

Abstract

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).<br /> (Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1521-3773
Volume :
51
Issue :
52
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
23161829
Full Text :
https://doi.org/10.1002/anie.201207307