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Synthesis and peptide coupling of protected 2-pyrrolylalanine

✍ Scribed by Aurélie A. Dörr; William D. Lubell

Book ID
104098645
Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
283 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

a b s t r a c t 2-Pyrrolylalanine has been synthesized in two protected forms and applied in the solution-phase synthesis of a dipeptide. (2S)-N-(Boc)-N 0 -(phenylsulfonyl)-and (2S)-N,N 0 -bis-(phenylsulfonyl)-3-(2-pyrrolyl)alanines (7 and 9) were obtained, respectively, in 14% and 13% overall yields and six and seven steps from oxazolidine b-methyl ester 1, which was derived from L-aspartic acid. Homoallylic ketone 2 was obtained from a copper-catalyzed cascade addition of vinylmagnesium bromide to 1 and converted into pyrrolylalanines 7 and 9 by a sequence featuring subsequent olefin oxidation and Paal-Knorr condensation. Protected pyrrolylalanine 9 was then introduced into a dipeptide.

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