Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 17, Pages 5079-5083Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201411350
Keywords
biomimetic synthesis; dipolar cycloaddition; polyphenols; racemic natural products; total synthesis
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Funding
- Direct For Mathematical & Physical Scien [1361807] Funding Source: National Science Foundation
- Division Of Chemistry [1361807] Funding Source: National Science Foundation
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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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