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  • Title: An asymmetric synthesis of aza analogues of the tricyclic skeleton of daphnane and the ABC ring system of phorbol.
    Author: Marson CM, Pink JH, Hall D, Hursthouse MB, Malik A, Smith C.
    Journal: J Org Chem; 2003 Feb 07; 68(3):792-8. PubMed ID: 12558400.
    Abstract:
    An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.
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