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A novel approach to periplanone-B involving an intramolecular Diels-Alder reaction with furan-diene and allene-dienophile



A novel approach to periplanone-B involving an intramolecular Diels-Alder reaction with furan-diene and allene-dienophile



Tetrahedron Letters 29(49): 6501-6504



The 6-step sequence to trienone, a known intermediate for the total synthesis of periplanone-B (a component of the sex pheromone of Periplaneta americana), involves the conversion of an acid into furan-allene using dilithiated propadiene, the IMDA of furan-allene to 2 exo-adducts, the conversion of one of these to a diol via a radical anion promoted cleavage of the oxygen bridge, and a in-situ low temperature Grob fragmentation to trienone.

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Accession: 001740363

Download citation: RISBibTeXText

DOI: 10.1016/s0040-4039(00)82384-9



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