Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 12, Issue 24, Pages 6403-6411Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200600136
Keywords
cobalt; hybrids; natural products; Nicholas reaction; synthesis
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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)]-enytic 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-al-kaloid or homohybrids can be accessed in totally stereo-, regio- and site-selective fashion. Ibis 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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