Beilstein J. Org. Chem.2021,17, 2781–2786, doi:10.3762/bjoc.17.188
Bratislava, Radlinského 9, 81237 Bratislava, Slovak Republic 10.3762/bjoc.17.188 Abstract A new highly diastereoselective synthesis of the polyhydroxylated pyrrolidine alkaloid (±)-codonopsinolB and its N-nor-methyl analogue, starting from achiral materials, is presented. The strategy relies on the trans
hydrogen peroxide catalyzed by phosphotungstic heteropoly acid. Each of the key reactions proceeded with an excellent diastereoselectivity (dr > 95:5). (±)-CodonopsinolB was prepared in 10 steps with overall 8.4% yield. The antiproliferative effect of (±)-codonopsinolB and its N-nor-methyl analogue was
evaluated using several cell line models.
Keywords: alkaloids; antiproliferative effect; codonopsinolB; diastereoselectivity; pyrrolidines; Introduction
CodonopsinolB (1) is a polyhydroxylated pyrrolidine alkaloid isolated from the roots of the plant Codonopsis pilosula (Figure 1) [1]. This compound was
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Graphical Abstract
Figure 1:
(−)-Codonopsinol B (1) and its N-nor-methyl analogue 2; known inhibition activities against α-gluco...