Synthesis and revision of the relative configuration of glabramycin B. Issue 45 (4th November 2015)

• Record Type: Journal Article
• Authors: Ishigami, Ken; Yamamoto, Masaoki; Watanabe, Hidenori
• Is Part Of: Tetrahedron letters. Volume 56:Issue 45(2015)
• Page Start: 6290
• Page End: 6293
• Publication Date: 2015-11-04
• Subjects: Glabramycin B -- Ten-membered lactone -- Antibiotics -- Determination of the relative configuration -- Sch 642305; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.149
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The stereostructure of glabramycin B, which is an antibacterial 10-membered lactone fused with 4-oxygenated cyclohexanone, was presumed on comparison with related compounds, and concise synthesis of our proposed structure of glabramycin B was achieved via dianion alkylation, Shiina's lactonization, and Stille cross coupling. We succeeded in the reassignment of its relative configuration.