De novo formal synthesis of (-)-apicularen A via an iterative asymmetric hydration sequence |
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Authors: | Li Miaosheng O'Doherty George A |
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Affiliation: | Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA. |
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Abstract: | [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. |
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