RuO4-promoted oxidative polycyclization of isoprenoid polyenes. A further insight into the stereochemistry of the process |
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| Authors: | Giuseppe BifulcoTeresa Caserta Luigi Gomez-Paloma Vincenzo Piccialli |
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| Institution: | a Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli ‘Federico II’, Via Cynthia 4, 80126 Napoli, Italy
b Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano (Salerno), Italy |
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| Abstract: | Further studies on the RuO4-catalyzed oxidative polycyclization of isoprenoid polyenes have been carried out. The configuration of the tris-THF product from the oxidation of geranylgeranyl acetate has been determined by a combination of spectral and chemical correlation methods. The oxidation of (E,Z)-farnesyl acetate, synthesized from nerol, has been carried out. This process stops at the first cyclization indicating that an E configuration of the Δ6 double bond is needed for the second cyclization to occur. The results are discussed in comparison with previous knowledge on the related Re(VII) polycyclization of polyenic bis-homoallylic alcohols. |
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| Keywords: | RuO4 oxidative polycyclization isoprenoid polyenes tris-THF configuration (E Z)-farnesyl acetate |
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