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Syntheses Nouvelles DE LA Mevalonolactone Marquee Au 14C, 13C, 3H - (RS) Mevalonolactone (14C-3′) et (RS) Mevalonolactone (3H-3′)

✍ Scribed by Bernard Rousseau; Jean-Pierre Beaucourt; Louis Pichat

Publisher
John Wiley and Sons
Year
1983
Tongue
French
Weight
536 KB
Volume
20
Category
Article
ISSN
0022-2135

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✦ Synopsis

Two procedures are described f o r the two s t e p synthesis o f I 3f-14c_]

mevalonolactone and H-methyl mevalonolactone from radioactive methyl magnesium iodide. The f i r s t route involves the addition of radiolabeled methyl mgnesiwn iodide with 1-12,4,10 t r i o x a adamantyl) 4 -t r i t y l o q 2-butanone : 2 followed by hydrolysis with acid. The overall y i e l d from methyl iodide was 37 % : s p e c i f i c a c t i v i t y 49 mCi/mMoZ.

c3-I3q mevalonic acid was prepared by t h e same technique a t a s p e c i f i c a c t i v i t y o f :

3.8 Ci/mMoz. f i e second route r e l i e s on t h e addition o f radiolabeled methylmagnesium

iodide upon I , I-dimethoxy 5-(2-tetrahydropyranyloxy~-3-pentanone : 2 followed by t h e oxidative hydrolysis of the reaction product with bromine-water-hydrochloric acid.

The overall y i e l d was 40 % from methyl iodide : s p e c i f i c a c t i v i t y : I mCi/mMol. The mlti s t e p synthesis of synthons : 5 and 2 are f u l l y described.

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