Synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone E from a common synthetic intermediate

Abstract

Propargylic/allylic sulfides, obtained using α-chloro sulfides, are utilized for 1,4-diol synthesis in an iterative manner to create carbinol stereocenters.

Stereoselective Synthesis of the C1–C22 Carbon Framework of (−)-Amphidinolide K

“…Oxidation of the secondary hydroxyl to ketone 19 using IBX followed by Wittig olefination furnished sulfide 20 . Treatment of sulfide 20 with NCS afforded a chloro sulfide intermediate which on reaction with vinylzinc bromide yielded allyl sulfide 9 . The configuration at C16 was inconsequential because it was to be destroyed subsequently.…”

“…The C10–C11 and the C9–O bonds were envisioned to be created using an α-chloro sulfide intermediate. Thus, reaction of chloro sulfide obtained from sulfide 7 with the alkynylzinc bromide prepared from homopropargylic ether 8 furnished the propargylic sulfide 26 . Oxidation followed by [2,3] sigmatropic rearrangement afforded unsaturated ketone 27 which on reduction using ( R )-CBS reagent yielded alcohol 28 .…”

Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties

“…etc.). QPSs were obtained using this method from triphenylphosphine for n = 1 [39,40], 2 , 3 [39,40,45,47,[60][61][62][63][64][65][66][67][68][69][70], 4 [40,44,47,62,65,[71][72][73][74][75][76][77][78][79][80][81][82][83][84], 5 [45,55,61,62,65,67,[85][86][87][88][89][90][91][92][93][94]…”

Total Synthesis of Chlorinated Oxylipin Eiseniachloride B

“…[5][6][7][8][9][10][11][12][13][14] Furthermore, it has recently become clear that oxylipin is involved in the innate immunity of macroalgae, [15][16][17][18][19] and many research groups have thus focused on its complex structure and unique biological activity in various synthetic studies. [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] In 2003, Kimura and colleagues discovered the novel oxylipins that contain a chlorine or iodine atom during a bioassayguided investigation of the brown alga, Eisenia bicyclis. 36) Eiseniachlorides A and B (1 and 2) are C 18 oxylipin consisting of cyclopentane and a 14-membered lactone, which corresponds to chlorohydrin biosynthesized via the nucleophilic opening of chlorine atoms to the oxirane of ecklonialactones A and B (3 and 4) isolated from the brown algae, Ecklonia stolonifera, by Kurata et al 37) and from Egregia menziesii by Gerwick and colleagues 38) (Fig.…”