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Total Synthesis of rac ‐γ‐Indomycinone by Baker–Venkataraman Rearrangement
Author(s) -
Krohn Karsten,
TranThien Hoan Trang,
Vitz Jürgen,
Vidal Anne
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700015
Subject(s) - chemistry , cleavage (geology) , ether , acetylation , halogenation , transesterification , alcohol , stereochemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry , geotechnical engineering , fracture (geology) , engineering , gene
The total synthesis of racemic γ‐indomycinone ( rac ‐ 3 ) was achieved by Baker–Venkataraman rearrangement of ester 11 to the diketone 12 , acid‐catalyzed cyclization to the anthrapyranone 13 , followed by methyl ether cleavage and acetylation to 16 , selective bromination of the branched side chain with simultaneous S N 1‐type hydroxy substitution to 23 and transesterification to rac ‐ 3 . The corresponding γ‐indomycinone 11‐methyl ether ( rac ‐ 20 ) was prepared in a similar reaction sequence.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)