Synthesis of vinyl threo-9, 10-threo-12, 13-tetrahydroxystearates View Full Text


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Article Info

DATE

1967-11

AUTHORS

John L. O’Donnell, L. E. Gast, J. C. Cowan, W. J. DeJarlais, G. E. McManis

ABSTRACT

Methyl esters from vernonia oil containingcis-12,13-epoxy-cis-9-octadecenoate were reacted with acetone in the presence of a boron trifluoride catalyst to yieldtrans-12,13-0-isopropylidene-9-ene derivative I. Epoxidation of the unsaturation followed by reaction with acetone gave the isomerictrans,trans-di-0-isopropylidene deriva-tivesIII of 9,10 :12,13-tetrahydroxystearates. The carboxylic acids of III were converted to vinyl esters and subsequent hydrolysis of the isopropy-lidene groups with boric acid produced vinylthreo-9,10threo-12,13-tetrahydroxystearates. By the same sequence of reactions monoepoxidized methyl linoleate yielded an optically inactive de-rivative which had identical refractive index, IR spectrum, and GLC data toIII from vernonia methyl esters. More... »

PAGES

652-655

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf02680036

DOI

http://dx.doi.org/10.1007/bf02680036

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1049736088


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