Quinone methides are typically reactive electrophilic species that are formed as transient reaction intermediates. However, in the presence of stabilizing structural elements, such as extended conjugation, stable quinone methides could be obtained. Indeed, a number of o-hydroxyl-p-quinone methide terpenoids, such as taxodione 1,   fuerstion 2,   celastrol 3   etc., were isolated from natural sources. The intriguing molecular structures and diverse biological activities of o-hydroxyl-p-quinone methide terpenoids attracted considerable attention. However, despite some early studies, efficient asymmetric synthetic routes to these terpenoids are yet to be developed. We embarked on developing a unified catalytic asymmetric approach to polycyclic o-hydroxyl-p-quinone methide terpenoids to enable access and biomedical studies of this family of natural products. Our recent progress along this line will be described.

Studies toward asymmetric synthesis of quinone methide terpenoids

245th National Meeting (2013)

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