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Synthesis of the Guaianolide Ring System via Cycloaddition of a Bicyclic Carbonyl Ylide with Allyl Propiolate

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journal contribution
posted on 06.08.2010, 00:00 by Vaidotas Navickas, Dmitry B. Ushakov, Martin E. Maier, Markus Ströbele, H.-Jürgen Meyer
A cyclic carbonyl ylide with a trans-annulated cyclopentane ring was generated by a Rh2(OAc)4-catalyzed reaction from a diazoketone precursor and trapped with allyl propiolate. The 1,3-dipolar cycloaddition led to the stereoselective formation of an oxygen-bridged polycycle. Via Curtius degradation, the cycloadduct was transformed to the ring skeleton typical of the sesquiterpene family of guaianolides.