An Efficient Synthesis of (±)-Grandisol Featuring 1,5-Enyne Metathesis

An eight-step synthesis of (±)-grandisol features a key sequence involving a high-yielding, microwave-assisted enyne metathesis to yield a 1-alkenylcyclobutene that is semihydrogenated to yield a silyl-protected grandisol. Metathesis catalyst screens revealed an intriguing trend whereby substrate co...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-01, Vol.75 (1), p.226-228
Main Authors: Graham, Thomas J. A, Gray, Erin E, Burgess, James M, Goess, Brian C
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Molecular Structure
Sex Attractants - chemical synthesis
Sex Attractants - chemistry
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
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Summary:An eight-step synthesis of (±)-grandisol features a key sequence involving a high-yielding, microwave-assisted enyne metathesis to yield a 1-alkenylcyclobutene that is semihydrogenated to yield a silyl-protected grandisol. Metathesis catalyst screens revealed an intriguing trend whereby substrate conversion correlated strongly with the identity of the ligands on the catalyst. In addition, new reactivity of 1-alkenylcyclobutenes toward hydrogenation is described.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9020375