Beilstein J. Org. Chem.2021,17, 2543–2552, doi:10.3762/bjoc.17.170
temperature and microwave power, although requiring much longer time. A possible mechanism for the cyclization is presented, and further functionalization of the newly created pyrrole ring in the dihydropyrrolizine core is described.
Keywords: dihydropyrrolizines; enaminones; microwaves; silica gel
products 19 thereafter proved to be easier as they are less polar than the enaminones, and could generally be separated from other byproducts. In these cases, overall isolated yields of the dihydropyrrolizines 19 are reported over the two steps.
The approximate time for completion of the cyclization of
under the cyclization conditions optimized for the formation of dihydropyrrolizines indeed produced the tetrahydroindolizine 26a, but in an extremely disappointing yield of less than 30%. Significant decomposition was noted even when the temperature was reduced. From some exploratory TLC studies it
PDF
Graphical Abstract
Figure 1:
Examples of 2,3-dihydro-1H-pyrrolizines (1–7) and 5,6,7,8-tetrahydroindolizines (8–10).
Beilstein J. Org. Chem.2020,16, 2776–2787, doi:10.3762/bjoc.16.228
(Nymphalidae: Danainae) have hairpencils on the forewings (i.e., androconia) that disseminate semiochemicals during courtship. While most ithomiines are known to contain derivatives of pyrrolizidine alkaloids, dihydropyrrolizines, or γ-lactones in these androconia, here we report on a new class of fatty acid
][12]. While dihydropyrrolizines are also used by other Lepidoptera, e.g., danaines [13][14][15] or arctiines [16][17], γ-lactones derived from necic acids are specific to ithomiines of more derived taxa [11].
Past studies of the androconia of Ithomia have reported the presence of 3 in Ithomia
PDF
Graphical Abstract
Figure 1:
Extended hairs (arrow) of the androconia of a male Ithomia salapia aquinia (Photo: Melanie McClure)....