The formation of the main skelton of bicyclomycin by the cyclization of 6-hydroxy-3-(3-hydroxypropyl)-2, 5-piperazinedione derivatives.

Y Sato, C Shin, S Sumiya, Y Nakajima…

Index: Sato; Shin; Sumiya; et al. Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 5 p. 1265 - 1270

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Citation Number: 5

Abstract

This paper describes the synthesis of 3-(3-t-butoxypropyl)-6-hydroxy-2, 5-piperazinedione derivatives by the hydroxylation of the corresponding 2, 5-piperazinedione with N- bromosuccinimide (NBS) in the presence of water and the subsequent cyclization to 2-oxa- 7, 9-diazabicyclo [4.2. 2] decane-8, 10-dione derivatives (11). The reversible interconversion between the spiro [oxolane-2, 2′-piperazine]-3′, 6′-dione prepared previously and the ...