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Synthesis of [16,16,17α-2H3] estradiol and [14α,15,15–2H3] estrone of high isotopic purity

✍ Scribed by Ian J. Massey; Laszlo Tökés

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
410 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The title compounds, each of high isotopic purity, were synthesized as internal standards for the mass spectral quantitation of estradiol and estrone. The [^2^H~3~] estradiol 3 was obtained from estrone (1) by alkaline H/^2^H exchange of the C‐16 protons and LiAl^2^LH~4~ reduction of the C‐17 keto function. The [^2^H~3~] estrone 16 was synthesized by a multistep sequence using deuterioboration of a C‐14 double bond and a three step reductive deuteration of a C‐15 keto function as the key steps for deuterium incorporation.

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