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Photochemistry of Tricyclo[5.2.2.02,6]undeca-4,10-dien-8-ones: An Efficient General Route to Substituted Linear Triquinanes from 2-Methoxyphenols. Total Synthesis of (±)-Δ9(12)-Capnellene

  1. Day-Shin Hsu Prof. Dr.1,2,
  2. Yu-Yu Chou2,3,
  3. Yen-Shih Tung2,
  4. Chun-Chen Liao Prof. Dr.2,3

Article first published online: 29 JAN 2010

DOI: 10.1002/chem.200902752

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 16, Issue 10, pages 3121–3131, March 8, 2010

Additional Information

How to Cite

Hsu, D.-S., Chou, Y.-Y., Tung, Y.-S. and Liao, C.-C. (2010), Photochemistry of Tricyclo[5.2.2.02,6]undeca-4,10-dien-8-ones: An Efficient General Route to Substituted Linear Triquinanes from 2-Methoxyphenols. Total Synthesis of (±)-Δ9(12)-Capnellene. Chem. Eur. J., 16: 3121–3131. doi: 10.1002/chem.200902752

Author Information

  1. 1

    Department of Chemistry and Biochemistry, National Chung Cheng University, Minhsiung (Taiwan), Fax: (+886) 5-2721040

  2. 2

    Department of Chemistry, National Tsing Hua University, Hsinchu 300 (Taiwan)

  3. 3

    Department of Chemistry, Chung Yuan Christian University, Chungli (Taiwan), Fax: (+886) 3-2653389

Publication History

  1. Issue published online: 1 MAR 2010
  2. Article first published online: 29 JAN 2010
  3. Manuscript Received: 6 OCT 2009

Funded by

  • National Science Council of Taiwan

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Keywords:

  • benzoquinones;
  • cycloaddition;
  • rearrangement;
  • total synthesis;
  • triquinanes

Abstract

An efficient and short entry to polyfunctionalized linear triquinanes from 2-methoxyphenols is described by utilizing the following chemistry. The Diels–Alder reactions of masked o-benzoquinones, derived from 2-methoxyphenols, with cyclopentadiene afford tricyclo[5.2.2.02,6]undeca-4,10-dien-8-ones. Photochemical oxa-di-π-methane (ODPM) rearrangements and 1,3-acyl shifts of the Diels–Alder adducts are investigated. The ODPM-rearranged products are further converted to linear triquinanes by using an O-stannyl ketyl fragmentation. Application of this efficient strategy to the total synthesis of (±)-Δ9(12)-capnellene was accomplished from 2-methoxy-4-methylphenol in nine steps with 20 % overall yield.

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