Stereoselective synthesis of the (−)-dysiherbaine furopyran core via BF3-promoted formal [3+2] annulation of aldehydo-aldoses with allylsilanes. Issue 48 (30th November 2016)

• Record Type: Journal Article
• Authors: Hotoda, Koki; Ohnuma, Asami; Kusakabe, Kosuke; Tanaka, Aki; Sasaki, Ikuo; Sugimura, Hideyuki
• Is Part Of: Tetrahedron letters. Volume 57:Issue 48(2016)
• Page Start: 5359
• Page End: 5362
• Publication Date: 2016-11-30
• Subjects: Tetrahydrofuran formation -- Allylsilane -- Chiral template -- Cyclization -- Fleming–Tamao oxidation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.10.073
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Formal [3+2] annulation of aldehydo -aldoses with allylsilanes is the key reaction. The THF ring of the dysiherbaine intermediate was stereoselectively constructed. The formation of the pyran ring was accomplished by cyclization of a triflate. Abstract: A highly stereoselective synthesis of the hexahydrofuro[3, 2- b ]pyran core of (−)-dysiherbaine is described. The key step in this synthesis includes the stereocontrolled formation of the tetrahydrofuran ring using the formal [3+2] annulation of the isopropylidene-protected aldehydo -L -arabinose and the β-substituted allylsilane mediated by trifluoroborane etherate.