Carbene and metal carbenoid species, originally viewed as too reactive to be useful for complex molecule
synthesis, have now emerged as attractive intermediates for the construction of highly functionalized heterocyclic
compounds. A popular route to metal carbenoids involves the decomposition of diazo starting materials, using
various transition metals. In this review we highlight some of the utilities of metal carbenoids in the synthesis
of biologically-active or natural product-like compounds. Some of the reaction classes that feature prominently in
these syntheses of alkaloids, described here, involve heteroatom/C-H insertion or cyclopropanation and 1,3-dipolar
cycloadditions. The facile constructions of fused ring systems via cascade reactions that encompass carbenoids are also discussed.
Keywords: Alkaloid, carbenoid, diazo, transition metals, ylide.
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