First Synthesis of Dialkyl Phosphonate Derivatives of Sesquiterpene α‐Methylene‐γ‐lactone.

Abstract

Terpenes Terpenes U 0200 First Synthesis of Dialkyl Phosphonate Derivatives of Sesquiterpene α-Methylene-γ-lactone. -[stereoselective synthesis and structure of two phosphorus-containing derivatives (III) of guaianolide arglabin (I)]. -(JALMAHANBETOVA, R. I.; RAKHIMOVA, B. B.; RALDUGIN*, V. A.; BAGRYANSKAYA, I. Y.; GATILOV, Y. V.; SHAKIROV, M. M.; KULYJASOV, A. T.; ADEKENOV, S. M.; TOLSTIKOV, G. A.; Russ. Chem. Bull. 52 (2003) 3, 748-751; Vorozhtsov Inst. Org. Chem., Sib. Branch Russ. Acad. Sci., Novosibirsk 630090, Russia; Eng.) -Staver 41-192

Arglabina – Lakton Seskwiterpenowy O Właściwościach Przeciwnowotworowych

“…W celu wzmocnienia działania przeciwnowotworowego badane są także fosforowe pochodne laktonu (Ryc. 6) [16]. Z fosfoorganicznymi pochodnymi związku wiązane są duże nadzieje.…”

Natural sesquiterpenoids

“…350, 351 The first synthesis of dialkyl phosphonate derivatives of a sesquiterpene ␣-methylene-␥ -lactone, arglabin, has been described. 352 Ligustolide A 357 and ligustolide B 358 are two novel sesquiterpenes, which possess a rare carbon skeleton probably formed by rearrangement of a 9,10-epoxy-guaianolide. 328 The and a seco-pseudoguaianolide, charminarone 370.…”

Synthesis and Biological Evaluation of Antitumor‐Active Arglabin Derivatives

“…Arglabin is assumed 17, 18 to prevent protein farnesylation without altering geranylgeranylation; thus, this compound inhibits post‐translational modification of ras protein in cells. Because of limited access to 1 , only a few derivatives of arglabin have been prepared 11, 19–21 so far. In this study, we set out to synthesize some more derivatives of 1 and to evaluate their antitumor activity.…”