Total synthesis of miltirone

One-pot ozonolytic synthesis of acyclic α,ω-bifunctional compounds from methyl 10-undecenoate and 10-undecen-1-ol

“…R f 0.20 (petroleum ether-methyl tert-butyl ether, 3 : 1). The 1 Н and 13 С NMR spectra are identical to those described in [34].…”

“…These acids can be virtually quantitatively converted into each other by acylation with the Ас 2 О-Ру system or by base hydrolysis (Scheme 7). Hydroxy acid 11 exhibits antibacterial and anti-infl ammatory properties and is used as a component of formulations for cosmetics and dermatology [27][28][29][30][31][32], acting as aldose reductase inhibitor, and of antidiabetic drugs [33]; in addition, it is the starting compound for the synthesis of a component of sex pheromone of Grapholitha molesta [34]. LEGOSTAEVA et al…”

Total synthesis of 1-oxomiltirone via Suzuki coupling

“…9 Furthermore, the additional application could synthesize miltirone by the reduction of the ketone group in 6, 5 de-methylation of the methyl ether and the subsequent Dess-Martin oxidation. 4 In conclusion, we have developed a short synthesis route to versatile intermediate 6 via Suzuki coupling as a key reaction. Its synthetic utility was demonstrated by the synthesis of 1-oxomiltirone.…”

“…Furthermore, methoxy group in C ring can be transformed into orthoquinone by demethylation of the methyl ether and subsequent oxidation. 4 We concluded that 6 could be a precursor of a A-B-C ring with different oxidative degree in the abietane diterpenes. Accordingly, the miltirone series of compounds could be synthesized through a key intermediate 6.…”

“…2 Due to their important activities, research has focused on the total syntheses of these compounds. [3][4][5] In our endeavor to modify bioactive abietane diterpenes for medical purposes, we found that compound 6 was a key intermediate to accomplish total synthesis of xanthoperyl methyl ether 2 and pisiferic acid 5.…”