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Stereocontrolled Synthesis of Carbon Chains Bearing Contiguous Methyl Groups by Iterative Boronic Ester Homologations: Application to the Total Synthesis of (+)‐Faranal
Author(s) -
Dutheuil Guillaume,
Webster Matthew P.,
Worthington Paul A.,
Aggarwal Varinder K.
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.200901194
Subject(s) - total synthesis , yield (engineering) , carbon chain , computer science , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , materials science , metallurgy
Adding links to the chain : A quadruple homologation of a boronic ester converts a simple vinyl iodide into a complex precursor to faranal with very high levels of diastereo‐ and enantiocontrol. This enables the synthesis of (+)‐faranal to be completed in just six steps and 18 % overall yield from propyne.