Biomimetic Total Synthesis of Santalin Y |
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| Authors: | Dr. Sebastian Strych Dr. Guillaume Journot Ryan P. Pemberton Dr. Selina C. Wang Prof. Dr. Dean J. Tantillo Prof. Dr. Dirk Trauner |
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| Affiliation: | 1. Department of Chemistry and Centre for Integrated Protein Science, Ludwig‐Maximilians‐Universit?t München, Butenandtstrasse 5‐13, 81377 München (Germany) http://www.cup.uni‐muenchen.de/oc/trauner/;2. Department of Chemistry, University of California‐Davis, 1 Shields Avenue, Davis, CA 95616 (USA) http://blueline.ucdavis.edu;3. Current address: UC Davis Olive Center (USA) |
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| 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. |
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| Keywords: | biomimetic synthesis dipolar cycloaddition polyphenols racemic natural products total synthesis |
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