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Asymmetric Total Synthesis of Fredericamycin A
Author(s) -
Kita Yasuyuki,
Higuchi Kazuhiro,
Yoshida Yutaka,
Iio Kiyosei,
Kitagaki Shinji,
Akai Shuji,
Fujioka Hiromichi
Publication year - 1999
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/(sici)1521-3773(19990301)38:5<683::aid-anie683>3.0.co;2-0
Subject(s) - total synthesis , absolute configuration , cycloaddition , stereospecificity , chemistry , stereochemistry , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis
Abstract Seventeen years after the isolation of the promising antitumor antibiotic fredericamycin A, the first asymmetric total synthesis of this compound has been accomplished and thereby its absolute configuration established. The key feature is the regiocontrolled [4+2] cycloaddition of 3 to 2 , which was obtained by the stereospecific rearrangement of 1 . Cp = (−)‐camphanoyl.