Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A
Research output: Contribution to journal › Journal article › Research › peer-review
Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vaticanol A has been achieved through three instances of quinone methide chemistry. These operations, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core, afforded a unique sequence for dihydrobenzofuran formation, and concurrently generated, in addition to the target molecule, a series of diastereomers reflective of many other isolates.
Original language | English |
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Journal | Angewandte Chemie International Edition |
Volume | 53 |
Issue number | 26 |
Pages (from-to) | 6747–6751 |
Number of pages | 5 |
ISSN | 1433-7851 |
DOIs | |
Publication status | Published - 2014 |
ID: 124781519