First enantioselective total synthesis of altersolanol A. Issue 41 (4th October 2018)

• Record Type: Journal Article
• Authors: Mechsner, Bastian; Henßen, Birgit; Pietruszka, Jörg
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 41(2018)
• Page Start: 7674
• Page End: 7681
• Publication Date: 2018-10-04
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob02113a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The first enantioselective total synthesis of altersolanol A was accomplished by Diels–Alder cycloaddition promoted by ( R )-3, 3′-BINOL/boron Lewis acid. Abstract : The first enantioselective total synthesis of altersolanol A, a secondary metabolite from the endophytic fungi Stemphylium globuliferum and Alternaria solani, is described. The key step towards the tetrahydroanthraquinone core was an asymmetric Diels – Alder (D–A) cycloaddition promoted by ( R )-3, 3′-diphenyl-BINOL/boron Lewis acid with good to excellent yields and excellent diastereo- and enantioselectivity (>95 : 5 dr and 98 : 2 er).