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  • Title: Total synthesis of (-)-stemoamide.
    Author: Torssell S, Wanngren E, Somfai P.
    Journal: J Org Chem; 2007 May 25; 72(11):4246-9. PubMed ID: 17451274.
    Abstract:
    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 beta,gamma-unsaturated azepine derivative 2 was obtained via a Pd(0)-catalyzed sp(2)-sp(3) 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.
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