TOTAL SYNTHESES OF (3S, 18S, 4E, 16E)-EICOSA-1,19-DIYNE-3,18-DIOL, (+)-DURYNE, (+)-DIDEOXYPETROSYNOL A, CICUTOXIN AND ATTEMPTS TOWARD THE TOTAL SYNTHESIS OF PETROSYNOL: POLYACETYLENIC POTENT ANTICANCER NATURAL PRODUCTS
(3S, 18S, 4E, 16E)-eicosa-1,19-diyne-3,18-diol, (+)-Duryne, Dideoxypetrosynol A, and Petrosynol are potent anticancer polyacetylenic alcohols with a variety of other interesting biological activities. The total syntheses of (3S, 18S, 4E, 16E)-eicosa-1,19-diyne-3,18-diol, (+)-Duryne, and Dideoxypetrosynol A, were accomplished utilizing double convergent synthetic approach. An auto-Wittig oxidation reaction was used as the key step in the institution of the central cis- double bond in the syntheses of (+)-Duryne and (+)-Dideoxypetrosynol A. The first enantioselective total synthesis of cicutoxin is reported. An endeavor toward the total synthesis of Petrosynol is also discussed.
School Location:USA - Ohio
Source Type:Master's Thesis
Keywords:enzymatic resolution lipase ak amano auto wittig oxidative coupling temporary silicon tethering ring closing metathesis
Date of Publication:01/01/2008