Grandisine alkaloids isolated from the leaves of Elaeocarpus grandis display affinity for human delta-opioid receptor. Although grandisine alkaloids (A-G) are attractive target molecules for total synthesis because of their structural diversity and pharmacological activity, only grandisine A has been synthesized so far. Hence, we undertook synthesis of other grandisine alkaloids via a flexible route applicable to various grandisine analogues as candidates of selective delta-opioid receptor agonist. We present here the first total synthesis of grandisine B, D and F employing highly stereoselective Br�nsted acid-mediated Morita-Baylis-Hillman reaction.

Total synthesis of grandisine B, D and F

239th National Meeting (2010)

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