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Synthesis of the 7-cis isomer of the natural leukotriene d4

✍ Scribed by I. Ernest; A.J. Main; R. Menassé

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
273 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

Methyl 5(S),G(S)-oxido-ll-oxo-7-c~~-9-~~an~-undecadienoate 2 was prepared and used for the synthesis of the novel 7-cib-LTD (9) as well as, after isomerization to the a&t-t&and dienal ester 2, for that40f-the natural leukotrienes.

In the pioneering synthesis by Corey et al.' of the optically active leukotriene A4 methyl ester I, the two Rhanb double bonds of the conjugated triene system were introduced in a two-step extension of the epoxy aldehyde ester 2 to the diene homolog 2 using the four-carbon reagent (1-lithio-4-ethoxybutadiene) 2 developed by Wollenberg .

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