Rotas sinteticas exploratorias a partir do acido L-(+)-tartarico e D-manitol

AUTOR(ES)
DATA DE PUBLICAÇÃO

1994

RESUMO

In the search for suitable intermediates for the synthesis in the near future of some chiral natural polyacetylenes isolated from Lobeliaceae (A) and Araliaceae (B, C), 16 compounds derived from L-(+)-tartaric acid (III, V, VI, XII, Xlll, XIV, XV, XVI, XVIII, XIX, XX, XXI, XXIl, XXIII, XXIV, XXV) and 13 from D-Mannitol (XXVI, XXVIl, IV, XXVIII, XXIX, XXX, XXXIl, XXXIV, XXXV, XXXVI, XXXVII, XLII, XLIII) were prepared Among the 29 compounds mentioned above, we note the new olefin (XXII) and the new chiral acetylenic alcohol (XLII). Both compounds contain fragments also found in the molecules of C-14 polyacetylenes from Lobeliaceae (a vicinal diol bonded to a carbon - carbon double bond) and of C-17 polyacetylenes from Araliaceae (a long chain propargylic alcohol). In order to test many of the reactions, we also prepared 05 compounds derived from isopropilidene glycerol (VIII, IX, X, XI, XXVlla), 1-phenylpropargilic alcohol to verify the efficiency of lithium acetylide generated in situ and 1, 2-epoxyoctane to test the alkynylation reaction through the epoxide opening. The molecular structures were characterized based upon the respective spectrar data (IRH NMR C NMR and MS). The new acetyrenic arcohor (XLIl) showed activity against Escherichia coli (ATCC 2592), when tested by monitoring the CO2 released during microbial respiration using FIA system. Finally we must say that this work is pioneering for the research group dedicated to the chemistry of natural polyacetylenes in the Chemistry Institute at UNICAMP.

ASSUNTO(S)

espectrometria de massa estereoquimica acido tartarico

ACESSO AO ARTIGO

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