123086-03-3Relevant articles and documents
Synthesis of Vinyl Sulfide Analogs of 2,3-Oxidosqualene and Their Inhibition of 2,3-Oxidosqualene Lanosterol-Cyclases
Zheng, Yi Feng,Dodd, Dharmpal S.,Oehlschlager, Allan C.,Hartman, Peter G.
, p. 5255 - 5276 (1995)
Syntheses of all trans(6E)-5-, (10E)-9-, (14E)-16- and (18E)-20-thia-2,3-oxidosqualenes as inhibitors of 2,3-oxidosqualene-lanosterol cyclase (OSC) are reported.To mimic the natural geometry of 2,3-oxidosqualene (2,3-OS), we required E-vinyl sulfides which were prepared by condensation of sulfur-substituted Wittig-Horner reagents (α-thioterpenoidyl diphenylphosphine oxides) with appropriate aldehydes.Mixtures of syn and anti α-hydroxydiphenylphosphine adducts were seperated by chromatography and the syn isomers were transformed to the E-vinyl sulfides.Both (6E)-5- and (18E)-20-thia-2,3-OS inhibited OSC from Candida albicans (IC50 = 47 and 0.2 μM, respectively) and rat liver (IC50 = 7.7 and 0.32 μM, respectively).Their activities were compared with those of previously synthesized (6E)-8- and (14E)-13-thia-2,3-Oss (IC50 = 0.68 and 45 μM, C. albicans, IC50 = 34 and 61 μM, rat liver, respectively).The best inhibitor among these compounds for the OSC of C. albicans and rat liver is the (18E)-20-thia-2,3-OS.This result suggests that modification of C-20 region of the 2,3-OS skeleton is an attractive strategy for development of OSC inhibitors.
First total synthesis of (±)-13-hydroxyneocembrene
Xing, Yacheng
, p. 595 - 600 (2007/10/03)
First total synthesis of (±)-13-hydroxyneocembrene (1), starting from 6-methyl-5-hepten-2-one (6) and geraniol (7), is described. The key steps are (i) the addition of sulfur-stabilized carbanion 12 to aldehyde 9, (ii) the synthesis of 18 by using phase-transfer catalyzed coupling reaction, and (iii) low-valent titanium-induced intramolecular coupling of oxo aldehyde 3 to afford the target molecule after the final deprotection.
Total synthesis of (+)-curacin A, a marine cytotoxic agent
Hoemann, Michael Z.,Agrios, Konstantinos A.,Aube, Jeffrey
, p. 11087 - 11098 (2007/10/03)
The total synthesis of curacin A, a cytotoxic agent that interacts with the colchicine binding site on tubulin, is described. The convergent synthesis utilizes natural product and chiral pool starting materials (geraniol, serine) and asymmetric synthesis
Total synthesis of curacin A
Hoemann, Michael Z.,Agrios, Konstantinos A.,Aube, Jeffrey
, p. 953 - 956 (2007/10/03)
Curacin A (1) was synthesized in a convergent manner. The key steps were (1) a Julia coupling to establish the stereochemistry of the C(7-10) diene, (2) a Wittig reaction to establish the stereochemistry of the C(3-4) alkene, and (3) a dehydrative cyclization to form the thiazoline ring system.
