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Total Synthesis of (−)-Stemoamide

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journal contribution
posted on 25.05.2007, 00:00 by Staffan Torssell, Emil Wanngren, Peter Somfai
A stereocontrolled total synthesis of (−)-stemoamide (1) is presented. The synthesis starts from commercially available (S)-pyroglutaminol (4). A chemoselective iodoboration of 5 was used to access key intermediate 3. The β,γ-unsaturated azepine derivative 2 was obtained via a Pd(0)-catalyzed sp2−sp3 Negishi cross-coupling using a Reformatsky nucleophile followed by a ring-closing metathesis reaction. The required C8−C9 trans-stereochemistry of 1 was accessed through a stereoselective bromolactonization/1,4-reduction sequence.