Synthesis p. 132 - 140 (1992)
Update date:2022-08-05
Topics:
Quimpere
Ruest
Deslongchamps
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- methylcyclotride-ca-3,9,11-triene (26) and (38) which led to tricyclic compound (cis-anti-cis)-2-methoxy-4,4,11,11-tetrakis(methoxycarbonyl)-1- methyl-tricyclo[7.4.0.02,6]tridec-7-ene (27) by transannular Diels-Alder reaction. Macrocyclization of trans-trans-trans chloride 46 was not successful.
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