The nicholas approach to natural product hybrids |
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Authors: | Alvaro Elsa de la Torre María C Sierra Miguel A |
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Institution: | Instituto de Química Orgánica, Dpto. de Productos Naturales, CSIC, C/Juan de la Cierva 3, 28006 Madrid, Spain. |
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Abstract: | The intermolecular Nicholas reaction of terpene-based scaffolds is an excellent access to natural product hybrid compounds. These intermolecular reactions have a low selectivity and are scarcely efficient for non-conjugated cations, but they are highly efficient to produce new terpene structures through an intramolecular reaction pathway. The use of cations derived from natural product derived Co(2)(CO)(6)]-enyne complexes is, in contrast, a highly efficient regio- and stereoselective procedure to prepare very complex structures, incorporating diverse densely functionalized or labile moieties. Thus, beta-pinene-diterpene-alkaloid or homohybrids can be accessed in totally stereo-, regio- and siteselective fashion. This approach efficiently discriminates between different propargylic positions by selecting the nature of the alcohol, being the enyne-derived cations the most reactive. The chimera 38 with a steroid-terpene-indole skeleton was prepared in this way. |
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Keywords: | cobalt hybrids natural products Nicholas reaction synthesis |
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