Cyclic hydroboration of geraniol derivatives: a synthesis of the left-hand portion of X-14547A

1 April 1986

journal article
research article
Published by Canadian Science Publishing in Canadian Journal of Chemistry

Vol. 64 (4) , 803-807
https://doi.org/10.1139/v86-132

Abstract

The stereochemical consequences of the cyclic hydroboration–oxidation of geraniol derivatives have been examined; moderately high selectivity (85–88%) for the formation of one major diastereomer has been observed, presumably as a consequence of remote asymmetric induction in the cyclic hydroboration of these 1,5-dienes. An approach to the synthesis of the left-hand portion of the ionophore antibiotic X-14547A is described.

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Total synthesis of the ionophore antibiotic X-14547A (Indanomycin)
The Journal of Organic Chemistry, 1984
Absolute configuration of (−)-4-methylheptan-3-ol, a pheromone of the smaller european elm bark beetle, as determined by the synthesis of its (3R,4R)-(+)- and (3S,4R)-(+)-isomers
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