Details

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

by Omollo, Ann Ondera

Abstract (Summary)
(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.
Bibliographical Information:

Advisor:

School:Miami University

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

ISBN:

Date of Publication:01/01/2008

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