Stereocontrolled Synthesis of Carbon Chains Bearing Contiguous Methyl Groups by Iterative Boronic Ester Homologations: Application to the Total Synthesis of (+)‐Faranal | Zendy

Dutheuil Guillaume | Zendy; Webster Matthew P. | Zendy; Worthington Paul A. | Zendy; Aggarwal Varinder K. | Zendy

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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.

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