Enantioselective Total Synthesis and Structure Confirmation of the Natural Dimeric Tetrahydroxanthenone Dicerandrol C. Issue 10 (25th January 2017)

• Record Type: Journal Article
• Authors: Ganapathy, Dhandapani; Reiner, Johannes R.; Valdomir, Guillermo; Senthilkumar, Soundararasu; Tietze, Lutz F.
• Is Part Of: Chemistry. Volume 23:Issue 10(2017)
• Page Start: 2299
• Page End: 2302
• Publication Date: 2017-01-25
• Subjects: dicerandrols -- enantioselectivity -- heterocycles -- natural products -- Suzuki reaction; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201700020
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The first enantioselective total synthesis of natural dicerandrol C (1 c ) as its enantiomer containing a dimeric tetrahydroxanthenone skeleton is described starting from the enantiopure chromane6 which was obtained through a Wacker‐type cyclization with >99 % ee . For the formation of the dimeric skeleton a palladium‐catalyzed Suzuki reaction was used. The synthesis allowed the confirmation of the absolute configuration of the dicerandrols. Abstract : All natural : The first enantioselective total synthesis of a natural dicerandrol containing a dimeric tetrahydroxanthenone skeleton is described starting from an enantiopure chromane, which was obtained through a Wacker‐type cyclization with >99 % ee . For the formation of the dimeric skeleton a palladium‐catalyzed Suzuki reaction was used. The synthesis allowed an unambiguous proof of the absolute and relative configuration of the natural product.