Progress Toward the Total Synthesis of Salvadione-A and Related Diterpenoids

Author: Greene, Blake Bennet

Year: 2004

Degree: Master's thesis

Advisor: Stoltz, Brian M.

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/AAPZ-W246

Abstract

Herein, we report our progress toward the total synthesis of salvadione-A, a structurally complex triterpenoid isolated from Salvia bucharica. We document a model system of our tandem Claisen/Cope/Diels-Alder strategy. Additionally, we describe the evolution of our strategy toward the synthesis of three structurally related diterpenoids-coulterone, cyclocoulterone, and komaroviquinone--from a cyclopropanation/Friedel-Crafts route to an anionic homo-Fries/intramolecular Barbier cyclization pathway.

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