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Synthesis of an ecdysteroid inhibitor of ecdysone biosynthesis

✍ Scribed by Antony Mauvais; Charles Hetru; Bang Luu

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
178 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

The hydroboration-oxidation of a A5.7 pregnadiene leads to a A7 6a-hydroxyderivative. This is converted to an acetylenic analogue of ecdysteroids, which is an inhibitor of their biosynthesis in vitro.

Several acetylenic cholesteryl derivatives have been reported by our group to irreversibly inhibit ecdysone biosynthesis 1, 2 It was reasonable to assume that the cholesteryl nucleus was transformed into an ecdysteroid precursor by the biosynthetic enzymes before reaching its target, the C-22 hydroxylase, which was inactivated by the acetylenic function (Scheme 1).

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