Ascarosides

[DARBEN at MELIA.QUT.EDU.AU]

Here's one from the vaults . . . In the late 1950's, a group of French 
researchers (Claudine Fouquey, et al) published a number of papers where 
they finally elucidated the structure of Faure-Fremiet's "ascaryl 
alcohol", the lipid extracted from the eggs and female reproductive tract 
of ascarid nematodes. These were a group of three basic glycosidic 
structures which they named ascarosides A, B and C. The chemistry in these 
papers is fairly solid, and subsequent authors, such as Jezyk and 
Fairbairn expanded the work, showing that the TLC moieties identified as 
ascarosides A, B and C were mixtures of similar substances, with  
variations in chain length of glycones, etc. However, in 1973, Tarr and 
Schnoes published work which disagreed with the placement of the second 
hydroxyl group/glycosidic linkage in ascarosides B and C. Fouquey et al 
placed this at carbon 6, whilst the later authors placed it on the 
penultimate carbon, thus making the molecule symmetrical. My question 
(finally) is : has any subsequent work been done to confirm either the 
Fouquey, et al structure or the Tarr and Schnoes model. Both are 
reasonably solid pieces of work. Thanks for any replies.
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Peter Darben
QUT, Brisbane, Queensland, Oz
Still making the world safe from pigworms
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