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Total Syntheses of Lactonamycin and Lactonamycin Z with Late‐Stage A‐Ring Formation and Glycosylation
Author(s) -
Adachi Satoshi,
Watanabe Kana,
Iwata Yusuke,
Kameda Shunsuke,
Miyaoka Yoshihito,
Onozuka Masao,
Mitsui Ryo,
Saikawa Yoko,
Nakata Masaya
Publication year - 2013
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.201209205
Subject(s) - glycosylation , ring (chemistry) , polyketide , chemistry , cycloaddition , total synthesis , stereochemistry , combinatorial chemistry , computer science , world wide web , catalysis , organic chemistry , biochemistry , biosynthesis , enzyme
The highly oxygenated polyketide antibiotics, lactonamycin and lactonamycin Z were synthesized. The BCDEF ring system was constructed by a cycloaddition and a palladium‐catalyzed cyclization and a Bischler–Napieralski‐type cyclization was used for the formation of the A ring. The glycosylation of the aglycon with the appropriate sugar gave lactonamycin and lactonamycin Z.