First extracted from the sponge Dysidea frondosa in 1997, the frondosin family comprises five marine-derived sesquiterpenes A-E. Previous studies showed that frondosins A-E exhibit anti-cancer, anti-inflammatory, and anti-HIV properties; therefore, several synthetic pathways were proposed to acquire these compounds. To this date, only the syntheses of frondosin A, B, and C have been completed. Despite these successes, the total synthesis of frondosin D has proved an invincible challenge since no one has successfully synthesized this marine-derived compound. This research reported two synthetic approaches that have been investigated in the Ovaska lab in an effort to obtain the tetracyclic core structure of Frondosin D. The key overlap between the two pathways is the seven-membered ring tricyclic compound accessed via tandem cyclization/Claisen rearrangement sequence previously developed by the Ovaska group.
Vo, Binh, "Progression Toward the Total Synthesis of Frondosin D" (2023). Chemistry Honors Papers. 33.
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