Synthesis of tubuphenylalanine and epi-tubuphenylalanine via regioselective aziridine ring opening with carbon nucleophiles followed by hydroboration-oxidation of 1,1-substituted amino alkenes
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DOI: 10.1016/j.tet.2018.10.024
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 aziridine 4 ring opening with carbon nucleophiles followed by hydroboration of 1,1-substituted aminoalkene 3 using… read more here.
Keywords: ring opening; regioselective aziridine; opening carbon; aziridine ring ... See more keywords
Molecular Basis for Enzymatic Aziridine Formation via Sulfate Elimination.
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DOI: 10.1021/jacs.2c07243
Abstract: Natural products containing an aziridine ring, such as mitomycin C and azinomycin B, exhibit antitumor activities by alkylating DNA via their aziridine rings; however, the biosynthetic mechanisms underlying the formation of these rings have not… read more here.
Keywords: via sulfate; aziridine ring; aziridine; formation ... See more keywords
Alkylative Aziridine Ring-Opening Reactions
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DOI: 10.3390/molecules26061703
Abstract: In this study, the highly strained three-membered aziridine ring was successfully activated as the aziridinium ion by alkylation of the ring nitrogen with a methyl, ethyl or allyl group, which was followed by ring opening… read more here.
Keywords: aziridine ring; ring opening; opening reactions; alkylative aziridine ... See more keywords