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Enantioselective Total Syntheses of Grayanoid (-)-Mollfoliagein A and (-)-Rhodomollein XXV
Shu-Fei Du1, Yi-Peng Zhang1, Quan-Lin Wu1
1Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, Yunnan Characteristic Plant Extraction Laboratory, School of Pharmacy, Yunnan University, Kunming 650500, P. R. China.
Abstract:
Herein, we report the convergent total syntheses of (-)-mollfoliagein A and (-)-rhodomollein XXV, two highly oxygenated grayanoids featuring a synthetically challenging oxa-tricyclo[3.3.1.03.7]nonane structure unit. The characteristic 5/7/6/5/5 skeleton of mollfoliagein A was constructed in a single step from two fragments via a Stille carbonylative coupling/transannular oxa-Michael addition/vinylogous Knoevenagel condensation cascade. Other salient features are the C/D ring formation by reshaping the bicyclo[3.3.0]octene unit to the highly functional bicyclo[3.2.1]octane ring system and PPTS mediated procedure for converting (-)-mollfoliagein A to (-)-rhodomollein XXV.
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