Journal
ORGANIC LETTERS
Volume 12, Issue 15, Pages 3418-3421Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1012185
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- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
- DAAD
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A cyclic carbonyl ylide with a trans-annulated cyclopentane ring was generated by a Rh(2)(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.
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