Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine [jaspine B].
نویسندگان
چکیده
A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.
منابع مشابه
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A new enantioselective total synthesis of pachastrissamine (jaspine B) was achieved from a known alpha,beta-unsaturated aldehyde by utilizing Córdova's asymmetric epoxidation as the chirality-inducing step. The 2,3-cis stereochemistry of pachastrissamine was established via intramolecular epoxide ring opening of a gamma,delta-epoxy-alpha,beta-unsaturated ester intermediate coupled with oxy-Mich...
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عنوان ژورنال:
- The Journal of organic chemistry
دوره 72 16 شماره
صفحات -
تاریخ انتشار 2006