Asymmetric Total Synthesis of (+)‐Neooxazolomycin Using a Chirality‐Transfer Strategy. (3rd July 2019)

• Record Type: Journal Article
• Authors: Kim, Jae Hyun; Kim, Illan; Song, Yeonghun; Kim, Min Jung; Kim, Sanghee
• Is Part Of: Angewandte Chemie. Volume 131:Number 32(2019)
• Page Start: 11134
• Page End: 11138
• Publication Date: 2019-07-03
• Subjects: Alkaloide -- Asymmetrische Synthese -- Diastereoselektivität -- Naturstoffe -- Totalsynthese; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201906158
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The total synthesis of (+)‐neooxazolomycin was achieved from the amino‐acid d ‐serine. The efficiency of this approach is derived from the use of principles of memory of chirality and dynamic kinetic resolution in the intramolecular aldol reaction of a serine derivative to build the densely functionalized lactam framework and to install three contiguous stereocenters. The key intermediate was readily elaborated to the target natural product. Abstract : Chiralitätstransfer : Die Totalsynthese von (+)‐Neooxazolomycin gelang mit exzellenter Stereokontrolle. Die sechs Stereozentren im Fragment rechts wurden aus d ‐Serin durch eine Abfolge von Chiralitätstransferprozessen erzeugt. MOC=Chiralitätsgedächtnis, DKR=dynamische kinetische Racematspaltung.