95694-70-5Relevant academic research and scientific papers
Chiral Synthesis of Bicyclomycin and Diastereomeric Stereoselectivity of the Key Aldol Condensation
Yamaura, Masanori,Nakayama, Tadashi,Hashimoto, Hironobu,Shin, Chung-gi,Yoshimura, Juji,Kodama, Hisashi
, p. 6035 - 6042 (2007/10/02)
Optically pure bicyclomycin (1) was synthesized via aldol condensation of racemic 7,9-bis(p-methoxybenzyl)-5-methylene-6--7,9-diaza-2-oxabicyclodecane-8,10-dione (2) with 2,3-di-O-isopropylidene-2-C-methyl-L-glyceraldehyde (3).The major condensation product 4 was then N-de(p-methoxybenzyl)ated and O-deisopropylidenated simultaneously with CAN and O-de(tert-butyldimethylsilyl)ated with Bu4NF under finely optimized conditions, respectively, to give 1.The structures of three other diastereomers of 4 were elucidated through comparisonwith the products of the aldol condensation of optically pure 2 and 3.The compounds (+)-2 and (-)-2 were prepared by diastereomeric separation of the synthetic precursor of 2, i.e., 5,6-dihydroxy-7,9-bis(p-methoxybenzyl)-7,9-diaza-2-oxabicyclodecane-8,10-dione as its (-)-MTPA ester, followed by the previously established four-step conversion.The stereoselectivity of the aldol condensation was explained by the chair conformation-like transition states.
Stereocontrolled Total Synthesis of (+/-)- and (+)-Bicyclomycin
Williams, Robert M.,Armstrong, Robert W.,Dung, Jen-Sen
, p. 3253 - 3266 (2007/10/02)
The completely regio- and stereocontrolled total synthesis of bicyclomycin (1) is described in 12 chemical steps.A new carbon-carbon bond-forming reaction on 1,4-dibenzyl- and 1,4-bis(p-methoxybenzyl)-3,6-bis(2'-thiopyridyl)-2,5-piperazinediones (10 and 4
