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Title: Total synthesis of antibacterial dibromotyrosine derived alkaloid purpuramine-K
Authors: Reddy, S Malla
Srinivasulu, M
Venkateswarlu, Y
Keywords: Antibacterial activity
methyl carbamate
THP protected hydroxyl amine
Issue Date: Dec-2006
Publisher: CSIR
Series/Report no.: Int.Cl.<sup>8</sup> C07C
Abstract: The first total synthesis of a dibromotyrosine derived alkaloid purpuramine K <b style="">1</b> reported for possible anti-bacterial activity against gram<i style="">-</i>positive bacteria <i style="">viz:</i> S<i style="">taphylococcus aureus</i>,<i style=""> Bacillus subtilis</i>,<i style=""> Bacillus sphaericus </i>and<i style=""> </i>gram-negative<i style=""> </i>bacteria like <i style="">Chromobacterium violaceum</i>,<i style=""> Klebsiella aerogenes</i>, and <i style="">Pseudomonas aeruginosa </i>has been achieved.<i style=""> </i>The synthesis involves preparation of methyl-3-bromopropyl carbamate <b style="">6</b>, and Boc protected 2-[3,5-dibromo, 4-hydroxy phenyl] ethyl amine <b style="">13</b> which is followed by coupling of these two structural fragments to give corresponding ether <b style="">14</b>.<b style=""> </b>After deprotection of Boc group in compound <b style="">14</b>, it is reacted with 4-hydroxyphenyl pyruvic acid oxime derivative <b style="">17</b> using EDCI/HOBT to give compound <b style="">18</b>, which is further transformed to purpuramine K.<b style=""> </b>
Description: 2757-2762
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(12) December 2006]

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