Beilstein J. Org. Chem.2014,10, 194–208, doi:10.3762/bjoc.10.15
the developed strategy ended up failing in more complex and sterically demanding systems.
Keywords: B-seco limonoids; biology oriented synthesis; Ireland–Claisen rearrangement; natural products; tetranortriterpenoids; Introduction
B-seco limonoids are a family of more than 100 highly oxygenated
plant tetranortriterpenoids derived from the 4,4,8-trimethyl-17-furanylsteroid core structure I (Figure 1) [1][2][3]. Members of this natural product class, like 21-hydroxytoonacilide (1) [4][5] and prieurianin (2) [6][7][8][9][10][11][12][13][14][15][16] display antifeedant [6][7][17][18][19][20][21
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Graphical Abstract
Figure 1:
Structures of the 4,4,8-trimethyl-17-furanylsteroid core structure I and the representative B-seco ...