4.8 Article

Intramolecular Condensation via an o-Quinone Methide: Total Synthesis of (±)-Heliol

Journal

ORGANIC LETTERS
Volume 14, Issue 12, Pages 2929-2931

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol301092w

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Funding

  1. National Science Foundation [CHE-0806356]
  2. Direct For Mathematical & Physical Scien [0806356, 0840521] Funding Source: National Science Foundation
  3. Division Of Chemistry [0806356, 0840521] Funding Source: National Science Foundation

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An acid-catalyzed intramolecular [4 + 2] cycloaddition of a non-natural bisabolene is reported. The key cyclocondensation was developed to access cyclic sesquiterpenes from linear phenolic precursors by generating a reactive o-quinone methide intermediate to initiate a cascade reaction. The new method was applied to the first total synthesis of (+/-)-heliol.

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