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Synthesis 1992; 1992(1/2): 132-140
DOI: 10.1055/s-1992-34151
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Synthesis and Transannular Diels-Alder Reaction of a 13-Membered Macrocyclic Triene. A Synthetic Approach Towards the Tricyclic Part A.B.C.[6.6.5] of the Veratrum Alkaloids

Miguel Quimpère* , Luc Ruest, Pierre Deslongchamps
  • *Laboratoire de synthèse organique, Départment de chimie, Faculté des sciences, Université de Sherbrooke, Sherbrooke, Québec J1K 2R1, Canada
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Publication Date:
18 September 2002 (online)

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The syntheses of the acyclic triene cis-trans-trans (3Z, 9Z,11E)-13-chloro-3-methoxy-1,1,7,7-tetrakis(methoxycarbonyl) -4-methyltrideca-3,9,11-triene (25), and the corresponding trans-cis-trans (3Z,9E,11E) isomer 37, and trans-trans-trans (3Z,9E,11E) isomer, 46, are described. Compounds 25 and 37 furnished in good yield 13-membered macrocyclic compounds (3Z,9Z, 11E)- and (3Z,9E,11Z)-3-methoxy-1, 1,7,7-tetrakis(methoxycarbonyl)-4-methylcyclotrideca-3,9,11-triene (26) and (38) which led to tricyclic compound (cis-anti-cis)-2-methoxy-4,4, 11,11-tetrakis(methoxycarbonyl)-1-methyltricyclo[7.4.0.0.2,6]tridec-7-ene (27) by transannular Diels-Alder reaction. Macrocyclization of trans-trans-trans chloride 46 was not successful.