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Biomimetic Total Synthesis of Santalin Y
Author(s) -
Strych Sebastian,
Journot Guillaume,
Pemberton Ryan P.,
Wang Selina C.,
Tantillo Dean J.,
Trauner Dirk
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201411350
Subject(s) - stereocenter , natural product , total synthesis , sandalwood , intramolecular force , cycloaddition , stereochemistry , biomimetic synthesis , chemistry , cascade , friedel–crafts reaction , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , philosophy , chromatography , theology
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.