טכניון מכון טכנולוגי לישראל
הטכניון מכון טכנולוגי לישראל - בית הספר ללימודי מוסמכים  
M.Sc Thesis
M.Sc StudentTishin Yekaterina
SubjectStudies Toward Total Synthesis of Gelsedine
DepartmentDepartment of Chemistry
Supervisor Professor Alex.m Szpilman
Full Thesis textFull thesis text - English Version


Abstract

Gelsedine was isolated in 1953 by Marion from Gelsemium Sempervirens. Wenkert elucidated the structure in 1962. The natural product displays cytotoxic activity against A431 cancer cells.

It was envisioned to synthesize Gelsedine in 13 straightforward steps.

This project focused on the first key step, a tandem cyclopropanation-divinylcyclopropane rearrangement. The cyclization successfully provided the desired cycloheptene in 4 linear synthetic steps in 16% overall yield.