Synthesis of (±)-Aureol by Bioinspired Rearrangements

A bioinspired and sustainable procedure for the straightforward synthesis of (±)-aureol has been achieved in eight steps (14% overall yield) from epoxyfarnesol. The key steps are the titanocene(III)-catalyzed radical cascade cyclization of an epoxyfarnesol derivative and a biosynthetically inspired...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-02, Vol.80 (3), p.1866-1870
Main Authors: Rosales, Antonio, Muñoz-Bascón, Juan, Roldan-Molina, Esther, Rivas-Bascón, Nazaret, Padial, Natalia M, Rodríguez-Maecker, Roman, Rodríguez-García, Ignacio, Oltra, J. Enrique
Format: Article
Language:English
Subjects:
Biochemical Phenomena
Catalysis
Cyclization
Epoxy Compounds - chemistry
Farnesol - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
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Summary:A bioinspired and sustainable procedure for the straightforward synthesis of (±)-aureol has been achieved in eight steps (14% overall yield) from epoxyfarnesol. The key steps are the titanocene(III)-catalyzed radical cascade cyclization of an epoxyfarnesol derivative and a biosynthetically inspired sequence of 1,2-hydride and methyl shifts.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502841u