Synthesis of CDEF ring systems of hexacyclinic acid

Sadiq, Bilal (2024) Synthesis of CDEF ring systems of hexacyclinic acid. MRes thesis, University of Glasgow.

Abstract

Hexacyclinic acid is a polyketide isolated from Streptomyces cellulosae in 2000. It comprises a 5/6/5 fused ring system (A, B and C) connected to a bridged tricycle (D, E and F). Hexacyclinic has demonstrated some notable cytotoxic activities against cancer cells. CDEF ring system plays a crucial role in completing the synthesis of cytotoxic hexacyclinic acid. This strategy was proved to be more efficient than the previous one developed by our group. 4-Benzyl-3-propionylthiazolidine-2-thione 160 was prepared from (R)-phenylalanine through reduction, cyclisation, and nucleophilic substitution reaction. Additionally, 4-methylpenten-al 115 was also synthesised from ethyl 4- methylpent-4-enoate to yield an aldol 161, which was converted to aldehyde 162 over two steps and subsequently used to generate the DEF fragment in the next step.

• Item Type: Thesis (MRes)
• Qualification Level: Masters
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Prunet, Dr. Joelle
• Date of Award: 2024
• Depositing User: Theses Team
• Unique ID: glathesis:2024-84793
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 10 Jan 2025 14:38
• Last Modified: 10 Jan 2025 16:22
• Thesis DOI: 10.5525/gla.thesis.84793
• URI: https://theses.gla.ac.uk/id/eprint/84793