Synthesis of Enantiomerically Pure Anthracyclinones

Synthesis of Idarubicinone via Global Functionalization of Tetracene

“…Moreover, the need for tailored analogs has made anthracyclines the subject of rigorous investigation within the synthetic community. [14][15][16][17][18] Thus, many innovative pathways to the aglycon anthracyclines (anthracyclinones) have been established, all of which rely upon annulation to forge one of the rings (see Fig 2b). The most commonly employed unifying disconnection is C-ring annulation, achieved through cycloadditions, 19 cationic cyclizations, 20 or anionic processes 21 (Fig.…”

Yeast‐Mediated Stereoselective Synthesis

“…The reduction of dichlorofluoroacetophenone, however, proceeded with low selectivity and low yields [108]. Very interesting intermediates 8 and 9 for the total synthesis of anthracyclinones [109] have been obtained by reducing racemic 7 [110] using S. cerevisiae Sigma-YSC-1 ( Figure 21 showing an ee of excellent 99.4% [111].…”

Anthracyclinones from Micromonospora sp.

“…The observed long-range correlations of H-10 (δ 8. 19) with C-11 (δ 183.7) and C-13 (δ 38.4), of H-7 (δ 8.32) with C-6 (δ 182.9) and C-9 (δ 150.0), and of H-14 (δ 1.75) with C-9 indicated the position of the isopropyl group at C-9, as well as the carbonyl groups at C-6 and C-11 (C ring) (Figure 2). On the basis of these data, the structure of 2 was established as 4methoxy-9-propyltetracene-6,11-dione.…”

“…The synthesis and isolation of new enantiomerically pure anthracyclinone moieties is a key strategy for developing new anthracyclines with improved therapeutic efficacy and reduced cardiotoxicity. 19 Further studies are in progress to obtain the anthracyclines from the isolated anthracyclinones and also to characterize their mechanism of cytotoxic action.…”

“…In general the anthracyclines are 80- to 100-fold more active than their respective aglycones. , Indeed the anthracycline doxorubicin, used as positive control, was 141 and 69 times more active than 1 and 4 , respectively. The synthesis and isolation of new enantiomerically pure anthracyclinone moieties is a key strategy for developing new anthracyclines with improved therapeutic efficacy and reduced cardiotoxicity . Further studies are in progress to obtain the anthracyclines from the isolated anthracyclinones and also to characterize their mechanism of cytotoxic action.…”