title: Biomimetic total synthesis of santalin Y.
abstract: A biomimetic total synthesis of santalin Y, a structurally complex but racemic natural product, is described. The key step is proposed to be a (3+2) cycloaddition of a benzylstyrene to a "vinylogous oxidopyrylium", which is followed by an intramolecular Friedel-Crafts reaction. This cascade generates the unique oxafenestrane framework of the target molecule and sets its five stereocenters in one operation. Our work provides rapid access to santalin Y and clarifies its biosynthetic relationship with other colorants isolated from red sandalwood.
authors: Department of Chemistry and Centre for Integrated Protein Science, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München (Germany) http://www.cup.uni-muenchen.de/oc/trauner/
authors: Sebastian
authors: S
authors: Strych
authors: Guillaume
authors: G
authors: Journot
authors: Ryan P
authors: RP
authors: Pemberton
authors: Selina C
authors: SC
authors: Wang
authors: Dean J
authors: DJ
authors: Tantillo
authors: Dirk
authors: D
authors: Trauner
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings; C000604131:santalin Y
keywords: biomimetic synthesis; dipolar cycloaddition; polyphenols; racemic natural products; total synthesis