Stereoselective Synthesis of the β‐Amino Acid Moiety of Fijiolide A. Issue 6 (14th December 2018)

• Record Type: Journal Article
• Authors: Kurzawa, Timon; Kerste, Eric; Nikodemiak, Paul; Bothe, Daniel; Harms, Klaus; Koert, Ulrich
• Is Part Of: European journal of organic chemistry. Issue 6(2019)
• Page Start: 1261
• Page End: 1267
• Publication Date: 2018-12-14
• Subjects: C–H Amination -- Nitrene insertion -- Fijiolide A -- Amino acids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801623
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An enantioselective synthesis of the β‐amino acid moiety of fijiolide A is described. Starting from eugenol, two sulfamates could be obtained on gram scale as substrates for an enantioselective C–H amination using Rh2 ( R/S ‐nap)4 . Acylation and ring opening of the resulting oxathiazinanes, followed by stepwise oxidation of the corresponding amino alcohol and TES‐protection of the catechol gave rise to Cramer's amino acid fragment from the total synthesis of fijiolide A. Abstract : A stereoselective synthesis of the β‐amino acid moiety of the fijiolides was achieved using an intramolecular Du Bois' asymmetric C–H amination of a sulfamate.