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Synthesis of the C‐1027 Chromophore Framework through Atropselective Macrolactonization
Author(s) -
Inoue Masayuki,
Sasaki Takeo,
Hatano Suguru,
Hirama Masahiro
Publication year - 2004
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.200461428
Subject(s) - chromophore , steric effects , ring (chemistry) , aldehyde , acetylide , scheme (mathematics) , computer science , chemistry , stereochemistry , mathematics , organic chemistry , catalysis , mathematical analysis
Long‐range steric interactions of the protecting groups of the 1,5‐diol were harnessed for the successful atropselective macrolactonization (A) in the synthesis of the C‐1027 chromophore framework (see scheme). Subsequent LiN(SiMe 3 ) 2 /CeCl 3 ‐promoted acetylide addition to an aldehyde (B) in the setting of a rigid macrocycle formed the target nine‐membered ring system with a highly strained diyne.