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Furo quinoline alkaloids

The Rutaceae is one of the most interesting families in regard to alkaloid chemistry as well as the formation of fla-vonoids, mono-, sesqui-, and triterpenes, furocoumarins, and other secondary compounds (Waterman and Grundon, 1983). Many chemical features support the view that the Rutaceae is a distinct and homogenous group. Essential oils and coumarins are found in at least four subfamilies. Furo-quinoline alkaloids are essentially ubiquitous in the family, and acridones are common. [Pg.575]

Quinoline Alkaloids.— This section will deal with simple quinolines as well as the larger group of isopentenyl- and furo-quinolines. ... [Pg.96]

During the last decade, new alkaloids of this type have been isolated, methods of asymmetric synthesis have been developed, the absolute stereochemistry of a number of alkaloids has been established, and the mechanisms of certain rearrangement reactions of furo- and pyrano-quinoline alkaloids of the group have been studied. Additional pyrano-quinolines of the flindersine type have been discovered, and new methods of synthesis have been developed. Isopropyldihydrofuroquinoline alkaloids without a hydroxy group in the side chain are characteristic components of Lunasia species, but not much new work on this group has appeared recently. [Pg.110]

Flindersine (141) has been known for many years and provides an intriguing exception to the general experience that furo- and pyrano-quinoline alkaloids have a linear arrangement of the three rings. During the... [Pg.140]

Earlier theories of the biosynthesis of quinoline alkaloids found in the Rutaceae have been discussed in Volume IX of this treatise, and the first experimental results using radioactive tracers were also reviewed. Spenser and his collaborators showed that anthranilic acid is incorporated intact into dictamnine in Dictamnus albus and that C-10 and C-ll (cf. 328) are derived from C-l and C-2 of acetate, respectively (220). Matsuo et al. (221) demonstrated almost simultaneously that the quinoline ring of skimmianine in Skimmia japonica was formed similarly. Since then, the biosynthesis of furo- and isopropyldihydrofuroquinoline alkaloids has been studied intensively, with particular interest in the origin of the C2 and C5 side chains present at the 3-position of the quinoline ring of these alkaloids. [Pg.183]

Rutaceae contain a number of alkaloids which can be chemically classified as methoxylated furo[2,3-6]quinolines. Only a few members will be discussed in this section (B-53MI31700, B-59MI31700, B-60MI31700, B-67MI31700, B-73MI31701, B-79MI31700). [Pg.988]

The assignment of configurations supports the mechanisms proposed for some well-known reactions of furo- and pyranoquinoline alkaloids. Thus, balfourolone (103) is believed to be an artifact formed from 0-methyI-balfourodinium salt with aqueous base, and the (I ) configurations of both compounds are consistent with a mechanism involving nucleophilic reaction at the 2-position of the quinoline ring. Conversion of (—)-(K)-balfourolone (103) into (+)-( )-isobalfourodine (104) with aqueous acid occurs at the tertiary center without affecting the chiral center, as expected. [Pg.132]


See other pages where Furo quinoline alkaloids is mentioned: [Pg.148]    [Pg.148]    [Pg.224]    [Pg.86]    [Pg.140]   
See also in sourсe #XX -- [ Pg.52 , Pg.286 ]




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