A new strategy for synthesizing the steroids with side chains from steroidal sapogenins: synthesis of the aglycone of OSW-1 by using the intact skeleton of diosgenin

Analysis of antitumor active OSW‐1 and its analogues by liquid chromatography coupled with electrospray and atmospheric pressure chemical ionization quadrupole mass spectrometry

“…OSW‐1 exhibits low toxicity against normal cells but inhibits the growth of human malignant tumor cells and is 10–100‐fold more potent than clinically established anticancer agents such as mitomycin C, doxorubicin, camptothecin, and paclitaxel 2. These attractive bioactivities and its structural novelty have prompted synthetic and medicinal chemists to synthesize OSW‐13–5 and related analogues 6–11. As part of our continuing studies on the syntheses of physiologically active steroids,12–14 we focused on the synthesis of OSW‐1 and its analogues that have thiophene in the steroidal side chain.…”

Synthesis of a Highly Potent Antitumor Saponin OSW-1 and its Analogues

“…Tian's strategy for the aglycone of saponin OSW-1 (Xu et al, 2003) Tian's group obtained the aglycone of saponin OSW-1 by degradation of diosgenin 45, an easily available and cheap substrate (Figure 13). To open ring F, diosgenin was treated with PhSH in the presence of BF 3 *Et 2 O.…”

“…A few months later Yu et al published the first total synthesis of saponin OSW-1 (Deng et al, 1999) by coupling of the aglycone with the sugar part. New approaches for the synthesis of this natural product were presented by Jin's Jin, 2001a, 2002), Morzycki's (Morzycki and Wojtkielewicz, 2002) and Tian's (Xu et al, 2003) groups.…”

New Analogues of the Potent Cytotoxic Saponin OSW-1

“…Several research groups have described the synthesis of OSW-1 aglycone. [12][13][14][15] Numerous methods of saponin OSW-1 semisynthesis are also known, including coupling of the aglycone with the sugar moiety. 14,[16][17][18] Various analogues of OSW-1 have also been prepared and tested for cytotoxicity recently.…”