Novel, racemic or nearly-racemic antibacterial bromo- and chloroquinols and ?-lactams of the verongiaquinol and the cavernicolin type from the marine spongeAplysina (=Verongia)cavernicola
作者:Michele D'Ambrosio、Antonio Guerriero、Francesco Pietra
DOI:10.1002/hlca.19840670610
日期:1984.9.26
Both 1 and 1c proved to be racemic from NMR examination of their esterification products with (–)-methyl-oxyacetic acid, whilst 6 had a ca. 6% enantiomeric purity as shown by a 1H-NMR study of its monoacetate 6′ in the presence of a chiral shift reagent. These chiroptical data of the first chiral quinols from the Verongida and of 6 suggest phenol oxidative routes from tyrosine precursors for their formation
地中海海绵的丁醇提取物Aplysina(= Verongia)cavernicola给,通过反相HPLC,抗菌quinols(±)-3- bromoverongiaquinol(=(±)-3-溴-1-羟基-4-氧代-2- ,5-环己基-1-乙酰胺;1d)和(±)-3-溴-5-氯verongiaquinol(=(±)-3-溴-5-氯-1-羟基-4-氧代-2,5-环己氨酸-1-乙酰胺;1c)除其正式环化的产物5-氯己二烯-1-乙酰胺外;1c)除了其正式环化的产物5-氯曲霉素(= 5-cloro-3,3a,7,7aβ-tetrahydro-3aβ-hydroxy-2,6(1 H)-indoledione; 6),C(7)-致敏的7β-溴-5-氯卡维尼可林(= 7β-溴-5-氯-3,3a,7,7aβ-四氢-3aβ-羟基-2,6(1H)-吲哚二酮; 4a和7α-bromo-5- chlorocavernicolin