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A new practical method for the preparation of [3H6]-leukotrienes C4 and D4

✍ Scribed by Michel L. Belley; Yves Gareau; Robert J. Zamboni; David G. Ahern; Yang Hong

Publisher
John Wiley and Sons
Year
1995
Tongue
French
Weight
448 KB
Volume
36
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A new method for the synthesis of highly deuterated or tritiated leukotrienes was developed. The higher reactivity of a terminal alkene compared to a 1,2‐disubstituted one permitted the selective deuteration or tritiation of the diyne 14,15,19,19,20,20‐hexadehydro LTC~4~ triester 1. After hydrolysis, LTC~4~ was obtained in 36% overall yield. An average of seven deuterium or tritium atoms was incorporated and the specific activity of the tritiated LTC~4~ was greater than 180 Ci/mmol. 1 was obtained from the addition of glutathione to 14,15,19,19,20,20‐hexadehydro LTA~4~ ethyl ester which was the product of a Wittig reaction between (3,8‐nonanediyn‐1‐yl)triphenylphosphonium iodide and 5(S), 6(S), 7(E), 9(E) ethyl 5,6‐epoxy‐11‐oxo‐7,9‐undecadienoate.

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