Castoreum chemistry

Castoreum of beaver (Castor canadensis) function, chemistry and biological activity of its components. In Chemical Signals in Vertebrates, vol. 6, ed. R. L. Doty, and D. Muller-Schwarze, pp. 457-464. New York Plenum. 

The chemistry shown in Eq. (21) uses a / -amino selenide as a radical precursor. /S-Amido radical cyclizations in which y -amido selenides served as the radical precursors have also been reported. One example has been described within the context of an approach to the ABC-ring system of manzamine A [47]. Another appears in an efficient synthesis of indolizidine 72, a component of castoreum derived from the Canadian beaver scent gland (Eq. 22) [48]. It is notable that allylic strain plays a role in the latter free-radical cyclization, as the furyl residue undoubtedly occupies an axial site on the incipient tetrahydropiperidone ring. 

Kingston, B. H., 1965, The chemistry and olfactory properties of musk, civet, and castoreum, Int. Proceed. Sec. Int. Cong. Endocrinol., 209. 

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See also in sourсe #XX -- [ ]

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