AI Article Synopsis
- Intermolecular Nicholas reactions of terpene-based structures are effective for creating hybrid natural products, especially through intramolecular pathways despite low selectivity for non-conjugated cations.
- The use of natural product-derived [Co(2)(CO)(6)]-enyne complexes allows for efficient and selective construction of complex terpene structures with various functional groups.
- This method can differentiate propargylic positions based on alcohol choice, leading to the development of targeted compounds like the steroid-terpene-indole chimera.
Article 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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| http://dx.doi.org/10.1002/chem.200600136 | DOI Listing |
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