Applications of Olefination Reactions to Cassiol Synthesis

Abstract

Olefination reactions directed to the synthesis of cassiol from compounds 2-5 will be discussed.

Studies on a New Synthetic Route towards Cassiol

“…A careful analysis of the reaction mixture allowed us the identification of unchanged starting material and some products that suggested that lactol 3 would suffer a Canizzaro-type reaction under the olefination reaction conditions, indicating a low reactivity of the carbonyl group of 3 under these conditions, probably due to steric hindrance [4].…”

An Exercise on Structure Elucidation Based on a Tricky Aldol Reaction

“…This exercise is based on a tricky aldol reaction we came across during the development of a synthetic sequence towards cassiol (2)(3)(4). Cassiol, 1, has been isolated from Cinnamomum cassia Blume and exhibits antiulcer activity and attractive structural features (5,6).…”