A highly stereoselective intramolecular Diels–Alder reaction for construction of the AB ring moiety of bruceantin. Issue 10 (4th March 2015)

• Record Type: Journal Article
• Authors: Usui, Kenji; Suzuki, Takahiro; Nakada, Masahisa
• Is Part Of: Tetrahedron letters. Volume 56:Issue 10(2015)
• Page Start: 1247
• Page End: 1251
• Publication Date: 2015-03-04
• Subjects: Diels–Alder reaction -- Intramolecular -- Natural product -- Stereoselective -- Synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.139
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A highly stereoselective intramolecular Diels–Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds.