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Asymmetric Total Synthesis of Solandelactone E: Stereocontrolled Synthesis of the 2‐ene‐1,4‐diol Core through a Lithiation–Borylation–Allylation Sequence
Author(s) -
Robinson Anna,
Aggarwal Varinder K.
Publication year - 2010
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.201003236
Subject(s) - borylation , sequence (biology) , diol , total synthesis , ene reaction , class (philosophy) , stereoselectivity , core (optical fiber) , stereochemistry , chemistry , combinatorial chemistry , computer science , organic chemistry , artificial intelligence , catalysis , biochemistry , alkyl , aryl , telecommunications
A highly stereoselective , 13‐step synthesis of solandelactone E is reported which employs the lithiation–borylation–allylation sequence as the key step (see scheme). This synthetic method solves the problem of poor stereocontrol at C11 that had dogged many previous syntheses of this class of molecules.