Synthesis of tubuphenylalanine and epi-tubuphenylalanine via regioselective aziridine ring opening with carbon nucleophiles followed by hydroboration-oxidation of 1, 1-substituted amino alkenes. Issue 48 (29th November 2018)

• Record Type: Journal Article
• Authors: Reddy, Ramesh B.; Dudhe, Premansh; Chauhan, Priyanka; Sengupta, Sagnik; Chelvam, Venkatesh
• Is Part Of: Tetrahedron. Volume 74:Issue 48(2018)
• Page Start: 6946
• Page End: 6953
• Publication Date: 2018-11-29
• Subjects: Regioselective aziridine ring opening -- Grignard reaction -- Hydroboration -- 9-BBN -- Tubuphenylalanine -- epi-tubuphenylalanine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.10.024
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An efficient synthesis of N -Boc-tubuphenylalanine benzyl ester ( N -Boc-Tup-OBn, 1a ) and N -Boc- epi -tubuphenylalanine benzyl ester ( N -Boc- epi -Tup-OBn, 1b ) is reported herein. Regioselective aziridine4 ring opening with carbon nucleophiles followed by hydroboration of 1, 1-substituted aminoalkene3 using 9-BBN and subsequent oxidation in an alkaline medium are used as the key steps to provide N -tosyl 1, 4-aminoalcohols. The 1, 4-aminoalcohols are successfully transformed into the desired products with an overall yield of 23% for1a and 11% for1b over 8 consecutive steps separately. Graphical abstract: