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Re 2 O 7 ‐Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12‐Desmethyl Analogue
Author(s) -
Rohrs Tyler M.,
Qin Qi,
Floreancig Paul E.
Publication year - 2017
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.201705924
Subject(s) - chemistry , desmethyl , stereoselectivity , total synthesis , catalysis , stereochemistry , stereoisomerism , molecule , combinatorial chemistry , organic chemistry , biochemistry , metabolite
Abstract Re 2 O 7 catalysis effects efficient and stereoselective dehydrative cyclization reactions from monoallylic diols, with stereocontrol arising from thermodynamic equilibration. This method was applied to a rapid synthesis of the spliceosome inhibitor herboxidiene. The route was also utilized for the synthesis of an analogue that highlights the importance of a single methyl group in biasing the conformation in the acyclic region of the molecule.