Total Synthesis of (-)-Stemoamide
2007 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, no 11, 4246-4249 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2007. Vol. 72, no 11, 4246-4249 p.
Chemoselective iodoboration; Metathesis reaction; Reduction sequences; Alcohols; Derivatives; Reduction; Synthesis (chemical); Amides; alkaloid derivative; azepine derivative; glutamine derivative; palladium; pyroglutaminol; stemoamide; unclassified drug; article; catalysis; cross coupling reaction; drug structure; drug synthesis; reduction; Reformatsky reaction; ring closing metathesis; stereochemistry; Alkaloids; Azepines; Catalysis; Heterocyclic Compounds, 3-Ring; Lactones; Models, Molecular; Molecular Conformation; Molecular Structure; Stereoisomerism
IdentifiersURN: urn:nbn:se:kth:diva-7407DOI: 10.1021/jo070498oISI: 000246570200034PubMedID: 17451274ScopusID: 2-s2.0-34249812712OAI: oai:DiVA.org:kth-7407DiVA: diva2:12425
QC 201008202007-08-232007-08-232010-08-20Bibliographically approved