Document Type

Restricted

Advisor

Timo Ovaska

Publication Date

2025

Comments

Access to this paper is restricted to the Connecticut College campus.

Abstract

Frondosin D is a natural sesquiterpene hydroquinone belonging to the frondosins family consisting of frondosin A through E. This family of compounds was first isolated from marine sponge Dysidea frondose in 1997 and have been demonstrated to exhibit potent anti-inflammatory, anti-tumor, and anti-HIV activities. Though being a promising multifunctional drug candidate, no successful synthetic approach for frondosin D has been reported up to date. The Ovaska lab has been investigating two primary synthetic approaches, A-D-B-C and D-C-B-A, both of which employ a tandem 5-exo dig cyclization/Claisen rearrangement method to construct the key seven-membered ring tricyclic intermediate. This study focused on a variation of the previously proposed A-D-B-C pathway, aiming to circumvent the steric hindrance encountered after the formation of the seven-membered ring intermediate in the pursuit of the total synthesis of frondosin

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