De novo formal synthesis of (-)-apicularen A via an iterative asymmetric hydration sequence.
[Structure: see text] A de novo approach to the formal total synthesis of the macrolide natural product (-)-apicularen A has been achieved in 18 steps from achiral starting materials. Both the absolute and relative stereochemistries of apicularen A were introduced by a Sharpless asymmetric dihydroxylation, a pi-allyl-palladium catalyzed reduction, a stereoselective reduction, and a base-promoted transannulation to install the C-9 stereocenter.
Li
Miaosheng
M
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
O'Doherty
George A
GA
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D006900:Hydroxylation; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; C117813:apicularen A; D010165:Palladium