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Issue 15, 1996
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Asymmetric synthesis of moiramide B


The first asymmetric synthesis of Moiramide B 1 is achieved using lithium amide 4 and pyrrolidinone auxiliary 5; pyrrolidinone auxiliary 5 is used to create the novel (S)-2-methyl-N-benzyloxysuccinimide 15 which is subsequently acylated with the highly reactive tert-butoxycarbonyl-protected N-carboxanhydride of L-valine (Boc-Val-NCA) under strongly basic conditions, without racemization, while lithium amide 4 is used to synthesize homochiral D-β-phenylalanine tert-butyl ester 8.

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Article information

Chem. Commun., 1996, 1797-1798
Article type

Asymmetric synthesis of moiramide B

D. J. Dixon and S. G. Davies, Chem. Commun., 1996, 1797
DOI: 10.1039/CC9960001797

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