Abstract

Furo[3,4-c] pyranone is a unique bicyclic molecular structure found in bioactive sesquiterpene isobolivianine and in artificial cytotoxic stilbene derivatives. The structure of furo[3,4-c] pyranone is analogous to cyclopenta[c] pyran structure found in potent cytotoxic iridoids like catapol. Chiral substrates for intramolecular hetero-Diels-Alder (IHDA) reaction have been synthesized in yields ranging from 39% to 81%. These compounds undergo [4+2] cycloaddition via ambimodal/ bispericyclic process to give a mixture of furo[3,4-c] pyranone in yields ranging 40-70% and aryl tetralin lactone derivatives. Density functional theory (DFT) calculations have been performed to gain insight into the mechanism leading to the formation of these compounds. Podophyllotoxins are aryl tetralin lignans with great potential as lead compounds for anti-cancer and antibiotic agents. The bioactivity of these compounds is attributed to their unique stereochemistry that is not easy to synthesize. Chiral substrates for intramolecular dehydro-Diels-Alder (IDDA) reaction have been synthesized in moderate yields. These novel compounds have been used to synthesize aryl tetralin lactone cores by IDDA reaction. This work demonstrates the potential utility of asymmetric IHDA and IDDA reactions in the total synthesis of bioactive compounds featuring furo[3,4-c] pyranone core and aryl tetralin lactones found in anticancer podophyllotoxins.

Degree

PhD

College and Department

Physical and Mathematical Sciences; Chemistry and Biochemistry

Rights

https://lib.byu.edu/about/copyright/

Date Submitted

2023-12-18

Document Type

Dissertation

Handle

http://hdl.lib.byu.edu/1877/etd13079

Keywords

Furo[3, 4-c] pyranone, Podophyllotoxin, aryl tetralin lactone, Intramolecular hetero/styryl Diels-Alder

Language

english

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