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Stereochemical Dichotomy in Two Competing Cascade Processes: Total Syntheses of Both Enantiomers of Spiroxin A
Author(s) -
Ando Yoshio,
Tanaka Daisuke,
Sasaki Ryota,
Ohmori Ken,
Suzuki Keisuke
Publication year - 2019
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.201906762
Subject(s) - enantiomer , cascade , total synthesis , stereochemistry , chemistry , quinone , combinatorial chemistry , chromatography
The first total synthesis of the marine antibiotic spiroxin A has been achieved for both enantiomeric forms. The discovery of two competing cascade processes triggered by two orthogonal stimuli, photo‐irradiation or acid/base treatment, enabled the divergent conversion of a single chiral, nonracemic bis‐quinone into both enantiomers of an advanced intermediate en route to both (−)‐ and (+)‐spiroxin A. The mechanism of the enantiodivergence is discussed.