"Applications of asymmetric allylation reactions towards natural produc" by Philip R. Harsh

Semester

Fall

Date of Graduation

2008

Document Type

Thesis

Degree Type

MS

College

Eberly College of Arts and Sciences

Department

Chemistry

Committee Chair

George O'Doherty.

Abstract

A short asymmetric synthesis of (R)-(+)-Goniothalamin oxide was developed and synthesized using a Leighton asymmetric allylation reaction and Grubbs ring-closing metathesis. (R)-(+)-Goniothalamin oxide is a styryl lactone that exhibits anti-cancer activity against a variety of cancer cell lines including MCF-7, T47D, and MDA-MB-231. The methododology of asymmetric allylation is also demonstrated on intermediates of RK-397, which is a 32-membered oxopolyene macrolide with anti-cancer activity.

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