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Synthesis of arnebinol, an inhibitor of prostaglandin biosynthesis

✍ Scribed by Kenji Mori; Masayuki Sakakibara; Michiru Waku

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
129 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new ansa-type compound, arnebinoll, was synthesized. Arnebinol l_, isolated from Arnebia euchroma (Boraginaceae) as an inhibitor of prostlj aglandin biosynthesis, has an ansa-type monoterpenylbenzenoid structure. We report here a synthesis of this compound l_, accompanied with its regioisomer _2_. A key step of our synthesis involved the reductive allylation of benzoquinone 2) with an allyltin compound 3_, prepared from geranyl acetate in 6 steps. 3) Geranyl acetate was converted into Las reported previously. Silylation(&-BuMe2SiC1, TEA, DMAP, CH2C12)4j of Agave an acetoxy silyl ether 5_ (94.2% yield), which was hydrolized(K2C03, aq. MeOHj 5)

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to give a diol monosiiyi etherL(97.7% yieidj. Chlorination(MsCi, LiCl, s-coii-

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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