4.7 Article

1,6-Hydroolefination and Cascade Cyclization of p-Quinone Methides with Styrenes: Total Synthesis of (±)-Isopaucifloral F

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 17, Pages 10107-10119

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01401

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Funding

  1. DST-SERB [EMR/2015/001759]
  2. IISER Mohali

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A Lewis acid-catalyzed intermolecular 1,6-hydroolefination of p-quinone methides with styrenes leading to vinyl diarylmethanes and indenes has been developed. This protocol was also elaborated to the total synthesis of (+/-)-isopaucifloral F. Besides, interestingly, the reaction between 2-alkynylated p-quinone methides and styrenes provided a straightforward access to dihydrobenzo[a]fluorene derivatives in one pot with 100% atom-economy.

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