Taxamairin; Icetaxane; Heck reaction; natural product; total synthesis
Issue Date
2019-10
Publisher
WILEY-V C H VERLAG GMBH
Citation
CHEMISTRYSELECT, v. 4, no. 40, Page. 11926-11929
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.