Estudos de rotas sinteticas visando a obtenção de terpenos nitrogenados

AUTOR(ES)
DATA DE PUBLICAÇÃO

1987

RESUMO

The search of synthetic routes leading to chiral nitrogen-containing terpenes constitutes the main purpose of this work. The first part deals with the synthesis of chiral tetra-and pentacyclic indolosesquiterpene skeletons presenting the sesquiterpene moiety linked to carbon-2 of the indole unit. The indolosesquiterpene family consists of a small group of new secondary metabolites which were isolated from medicinal African species of Greenwayodendron (Annonaceae). A common key intermediate was visualized for the synthesis of tetra and pentacyclic indolosesquiterpenes. The proposed route to reach this basic skeleton envolved assembling a sesquiterpene moiety to an indole unit. Synthons 23b(1-methylene-2-oxo-5,5,8a-trimethyl-decahydronaphthalene), 25(1-[[(p-tolylsulfonyl)oxy]methyl]-2-oxy-5,5,8a-trimethyldecahydronaphthalene) and 26a (2-acetoxy-2,5,5,8a-tetramethyl-decahydro-1-naphthaleneacetic acid) were prepared using (+) manool 28 , geraniol 81 and sclareol 46 respectively, as starting material. The indolosesquiterpene key-intermediate was obtained by assembling the acyl chloride 26a to o-toluidine followed by the formation of the indole nucleus using Madelung s approach. The indolosesquiterpene skeleton 20b constitutes the first, example of synthesis of this class of compounds. The second part of our work describes our efforts towards a nitrogen atom introduction in a six membered ring of chiral mono and sesquiterpene skeletons using the N funtionalization ofan unactivated C-H bond using photochemical intramolecular reactions of amine derivatives and acyl azides. We have therefore used (-)b-pinene 134, (-)carvone 137 and perillic acid 166 as chiral templates. The apprapriate physical data of the synthesized compounds are reported.

ASSUNTO(S)

terpenios produtos sinteticos

ACESSO AO ARTIGO

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