Enantioselective total synthesis of altersolanol A and N. Issue 13 (1st July 2019)

• Record Type: Journal Article
• Authors: Mechsner, Bastian; Böse, Dietrich; Hogenkamp, Fabian; Ledermann, Nadia; Hartmann, Rudolf; Bochinsky, Kevin; Frey, Wolfgang; Pietruszka, Jörg
• Is Part Of: Bioorganic & medicinal chemistry. Volume 27:Issue 13(2019)
• Page Start: 2991
• Page End: 2997
• Publication Date: 2019-07-01
• Subjects: Natural product -- Asymmetric synthesis -- Enantioselectivity -- Diels-Alder reaction; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2019.04.033
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: The development of the first enantioselective total synthesis of altersolanol N is reported. The decisive step of the synthesis is the enantioselective formation of the tetrahydroanthraquinone nucleus by a [4 + 2]-cycloaddition in high yield and with excellent diastereo- and enantioselectivity (>95:5 dr and 95:5 er). In addition, a demanding selective monoacetylation of the OH group at the C-2 position was achieved: an epoxide ring opening with the participation of a neighbouring acetyl group could be established. The route proved to be an efficient alternative to also access enantiomerically pure altersolanol A.