Asymmetric Total Synthesis of (+)‐Neooxazolomycin Using a Chirality‐Transfer Strategy. Issue 32 (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 international edition. Volume 58:Issue 32(2019)
• Page Start: 11018
• Page End: 11022
• Publication Date: 2019-07-03
• Subjects: alkaloids -- asymmetric synthesis -- diastereoselectivity -- natural products -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201906158
• Languages: English
• ISSNs: 1433-7851

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 : Chirality transfer : The total synthesis of (+)‐neooxazolomycin was achieved with excellent stereocontrol. The six stereocenters in the right‐hand fragment were derived from d ‐serine by a series of chirality‐transfer processes. MOC=memory of chirality, DKR=dynamic kinetic resolution.