Total Syntheses of Spidamine and Joramine, Polyamine Toxins from the Joro Spider, Nephila clavata.

T CHIBA, T AKIZAWA, M MATSUKAWA…

Index: Chiba, Tadashige; Akizawa, Toshifumi; Matsukawa, Motomi; Nishi, Masatoshi; Kawai, Nobufumi; Yoshioka, Masanori Chemical and Pharmaceutical Bulletin, 1996 ,  vol. 44,  # 5  p. 972 - 979

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Citation Number: 13

Abstract

In order to confirm the structures of spidamine and joramine, identified from the venom of a spider (Nephila clavata), we convergently synthesized both compounds, which have a common side chain of N-(L-asparaginyl)-N'-(3-aminopropyl-β-alanyl)-1, 5-pentanediamine. A synthon of the common side chain was synthesized by starting with n-propanolamine which was converted to 7-azido-N-benzyloxycarbonyl-4-azaheptanoic acid N- ...