117268-79-8

Upstream product

• 64-17-5 ethanol 
• 1666-13-3 diphenyl diselenide 
• 16940-66-2 sodium tetrahydroborate 

Downstream Products

• 122080-54-0 Se-phenyl 2-(allyloxy)selenobenzoate 
• 122080-59-5 (S)-1-Allyl-5-oxo-pyrrolidine-2-carboselenoic acid Se-phenyl ester 
• 122080-55-1 Se-Phenyl 2-(Prop-2-enylthio)selenobenzoate 
• 53331-94-5 Boc-Phe-SePh 
• 27372-03-8 ethyl 3-hydroxy-2-methylbutyrate 
• 117668-89-0 diethyl 2-hydroxy-2-phenylselenomethyl succinate 
• 117668-85-6 3-Hydroxy-2-phenylselanyl-hexanoic acid ethyl ester 
• 199792-15-9 C₅₆H₇₆O₈SeSi₂ 
• 122080-61-9 (S)-3-Allylsulfanyl-2-benzyloxycarbonylamino-selenopropionic acid Se-phenyl ester 
• 122080-57-3 Se-Phenyl N-Acetyl-N-allylselenoanthranilate 

Relevant academic research and scientific papers

Total synthesis of Palmarumycin BGs, C1 and Guignardin e

The first total synthesis of Palmarumycin BG1-3, BG5-6, C1 and Guignardin E (1-7) were achieved by the same intermediate Palmarumycin C2 through a N-benzyl cinchoninium chloride-catalyzed epoxidation, an organoselenium-mediated reduction, and a cerium(iii) chloride hydrate-promoted regioselective ring-opening and elimination of cyclic α,β-epoxy ketone as the key steps via6-7 step routes using 1,8-dihydroxynaphthalene (DHN) and 5-methoxytetralone as the starting materials in overall yields of 1.0-17.4%, respectively. Their structures and absolute configurations were characterized and determined by 1H, 13C NMR, IR, HR-ESI-MS and X-ray diffraction data. These compounds displayed significant inhibition activities against HCT116, U87-MG, HepG2, BGC823 and PC9 cell lines.

Convergent total synthesis of gymnocin-A and evaluation of synthetic analogues

The first total synthesis of gymnocin-A (1), a cytotoxic polycyclic ether isolated from a notorious red tide dinoflagellate, Karenia mikimotoi, has been accomplished. The synthesis relies heavily on the Suzuki-Miyaura cross-coupling-based methodology to assemble the tetradecacyclic polyether skeleton. Convergent union of the GHI (5) and KLMN (6) rings, both of which were prepared from a common intermediate 7, and the subsequent ring closure of the J ring delivered the GHIJKLMN ring. The crucial coupling between the ABCD and FGHIJKLMN ring fragments (3 and 4, respectively) and stereoselective installation of the C17 hydroxyl group, followed by cyclization of the E ring gave rise to the tetradecacyclic polyether skeleton 2. Finally, incorporation of the 2-methyl-2-butenal side chain completed the total synthesis of gymnocin-A. The convergent nature of the synthesis, which employs three fragments of comparable complexity, is well-suited for preparation of various structural analogues of gymnocin-A to explore the structure-activity relationship. The results of preliminary structure-activity relationship studies of several synthetic analogues are also provided.

The organoselenium-mediated reduction of α,β-epoxy ketones, α,β-epoxy esters, and their congeners to β-hydroxy carbonyl compounds: Novel methodologies for the synthesis of aldols and their analogues

Novel methods for the reduction of α,β-epoxy ketones, α,β-epoxy esters (glycidic esters), and their congeners to β-hydroxy carbonyl compounds (aldols) by the use of organoselenium reagents are described. The reagents, a sodium phenylseleno(triethyl)borate complex Na[PhSeB(OEt)3] easily prepared by reduction of (PhSe)2 with NaBH4 in EtOH and benzeneselenol (PhSeH) generated in situ from the borate complex by addition of acetic acid, have been demonstrated to serve as excellent reducing agents for these transformations. The organoselenium-mediated reduction of α,β-epoxy carbonyl compounds regiospecifically occurs at the α-carbon to produce a wide variety of cyclic (intramolecular) aldols as well as acyclic (intermolecular) ones in excellent yields. Quantitative mechanistic studies have revealed that the organoselenium-mediated reduction proceeds via an α-substitution process in contrast to the common electron transfer reducing agents.