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

摘要

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 re- structuring 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.