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First Stereoselective Total Synthesis of FD‐594 Aglycon
Author(s) -
Masuo Ritsuki,
Ohmori Ken,
Hintermann Lukas,
Yoshida Saki,
Suzuki Keisuke
Publication year - 2009
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.200806338
Subject(s) - stereoselectivity , chemistry , intramolecular force , stereochemistry , diol , pinacol , nucleophile , total synthesis , lactone , xanthone , catalysis , organic chemistry
Stereocontrolled access to the hexacyclic core of FD‐594 has been achieved. The key steps include the intramolecular S N Ar reaction for construction of the densely functionalized xanthone skeleton, the stereoselective lactone cleavage using a chiral nucleophile to induce the axial stereochemistry, and the SmI 2 ‐mediated pinacol cyclization for the stereocontrolled conversion of axially chiral biaryl dialdehyde into the corresponding trans diol.