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

Abstract

An 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 beta,gamma-enedione intermediate. The beta,gamma-double bond has been introduced by the acid catalyzed water assisted elimination of a beta-tertiary alcohol. Later, the beta,gamma-enedione on introduction of requisite unsaturation transforms into Taxamairin B.