Generation of the Icetexane Core by Use of a Heck Strategy: Total Synthesis of Taxamairin B

Abstract

AbstractAn efficient approach towards the total synthesis of Taxamairin B has been accomplished within 6 steps starting from o‐bromobenzylbromide 7 with 45% overall yield. Intramolecular Heck reaction works efficiently to furnish the 6–7‐6 fused icetexane scaffold under hydrative condition, which on restructuring affords the key β,γ‐enedione intermediate. The β,γ‐double bond has been introduced by the acid catalyzed water assisted elimination of a β‐tertiary alcohol. Later, the β,γ‐enedione on introduction of requisite unsaturation transforms into Taxamairin B.