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Synthetic Studies on Dolabellane Diterpenoids. Synthesis of 10-epi-Clavudiol A, an Epimer of a Marine Dolabellanoid

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概要 In the line of our synthetic studies on the medium-ring containing higher terpenoids, we have applied our strategy, which is featured by obtaining a diterpenic skeleton from two monoterpene units, to ...the synthesis of the dolabellane family having a fused 5-11 bicyclic skeleton. From functionalized iridoid and geranyl synthons, 10-epi-clavudiol A, an epimer of marine dolabellane clavudiol A, has been totally synthesized. Noteworthy steps include a feasible isomerization of the more substituted double bond to the less substituted one via the reduction of the allylic chloride mediated by Cr(II)Cl_2 in the presence of alcoholic proton source and an intramolecular pinacol coupling to form the eleven-membered ring.続きを見る

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登録日 2009.04.22
更新日 2017.06.07