Synthesis of arphamenine A and epi-arphamenine A

Umezawa, H; Nakamura, T; Fukatsu, S; Agyagi, T; Tatsuta, K

HERO ID

4933588

Reference Type

Journal Article

Year

1983

HERO ID 4933588
In Press No
Year 1983
Title Synthesis of arphamenine A and epi-arphamenine A
Authors Umezawa, H; Nakamura, T; Fukatsu, S; Agyagi, T; Tatsuta, K
Journal Journal of Antibiotics
Volume 36
Issue 12 (1983)
Page Numbers 1787-1788
Abstract Arphamenine A, produced from Chromobacterium violaceum BMG361-CF4 as an amino peptidase B inhibitor, is the first naturally occurring carba analog of peptide and epi-arphamenine A is the artifact from the epimerization at C-2. Here the authors describe the synthesis of optically active arphamenine A and epi-arphamenine A. Since in these compounds epimerization at C-2 should be inevitable, the C-1 similar to C-3 portion was synthesized by "malonic ester synthesis" which gave the diastereomers.
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Dupe Override No
Is Public Yes
Keyword Chromobacterium violaceum