A short synthesis of (±)-13-deoxyserratine

Abstract : A short and efficient total synthesis of (±)-13-deoxyserratine (3) features a highly stereoselective intramolecular Pauson-Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %. THP = tetrahydropyranyl, TBS = tert-butyldimethylsilyl.
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J. Cassayre, Fabien Gagosz, Samir Zard. A short synthesis of (±)-13-deoxyserratine. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2002, 41 (10), pp.1783-1785. ⟨10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I⟩. ⟨hal-00954852⟩

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