Photochemistry of tricyclo[5.2.2.0(2,6)]undeca-4,10-dien-8-ones: an efficient general route to substituted linear triquinanes from 2-methoxyphenols. Total synthesis of (+/-)-Delta(9(12))-capnellene

Chemistry : a European Journal
Day-Shin HsuChun-Chen Liao

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[5.2.2.0(2,6)]undeca-4,10-dien-8-ones. Photochemical oxa-di-pi-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 (+/-)-Delta(9(12))-capnellene was accomplished from 2-methoxy-4-methylphenol in nine steps with 20 % overall yield.

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Citations

Oct 20, 2011·The Journal of Organic Chemistry·John R GoodellJohn A Porco
Oct 17, 2015·The Journal of Organic Chemistry·Chun-Chieh WangGary Jing Chuang
Apr 28, 2016·Chemical Reviews·Markus D KärkäsCorey R J Stephenson
Jan 21, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Davide RavelliAngelo Albini
Oct 31, 2018·Organic & Biomolecular Chemistry·Yuichiro KawamotoHisanaka Ito
Aug 3, 2011·Natural Product Reports·Braulio M Fraga
May 7, 2013·Natural Product Reports·Jonathan C Morris
Aug 24, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yi QiuLiu-Ping Chen
Jan 20, 2011·Angewandte Chemie·Thorsten Bach, Jörg P Hehn
Jul 5, 2013·The Journal of Organic Chemistry·Shou-Jie Shen, Wei-Dong Z Li

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