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; biologyorientedsynthesis; Ireland–Claisen rearrangement; natural products; tetranortriterpenoids; Introduction
B-seco limonoids are a family of more than 100 highly oxygenated
a trans-fused bicyclic C–D ring having an exo-methylene moiety. The crowded C9–C10 bond bridging the two domains is the main synthetic obstacle.
Taking into account the biology-orientedsynthesis (BIOS) concept [27][28][29][30][31][32][33][34], which employs the scaffolds of biologically relevant
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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 ...
Beilstein J. Org. Chem.2013,9, 775–785, doi:10.3762/bjoc.9.88
particular, play a key role in guiding the navigation of chemical space [2][3][4]. The field of biology-orientedsynthesis (BIOS) [5], for example, uses biologically validated scaffolds [6][7][8] to inspire library design.
Known organic molecules populate chemical space unevenly and unsystematically. Around
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Graphical Abstract
Scheme 1:
Illustrative examples of a synthetic approach to natural-product-like molecules with over eighty mo...