155489-00-2Relevant academic research and scientific papers
Formal synthesis of borrelidin: A highly enantio- and diastereoselective access to the Morken's C2-C12 intermediate
Gembus, Vincent,Karmazin, Lydia,Uguen, Daniel,Zoller, Thomas
, p. 359 - 380 (2019/02/25)
In contrast to methyl and isobutyl phenyl sulfone, condensing under basic conditions higher alkyl sulfones and trans-2,3-epoxy-butanol 13c (or its O-benzyl and O-silyl derivatives) proved unfeasible, a difficulty that was overcome by using mono ethers of trans-2,3-epoxy-butane-1,4-diol 35c as the electrophilic reagents. Thus, adding excess BuLi to a mixture of the benzyl ether 35b and sulfone ent-12a, a stereodiad sulfone prepared in pure state from the R-Roche ester, via the O-trityloxy-sulfone ent-12c (X-ray), gave, after elimination by column chromatography of the side-formed regioisomer, a diolsulfone that was next converted to sulfone 20 by means of conventional functional-group modifications. Reacting like-wise this sulfone with the parent O-PMB derivative 35a, and then proceeding to the same purification process and function adjustment, delivered the title fragment in virtually pure state.
Total synthesis of haliclamide
Gahalawat, Suraksha,Pandey, Satyendra Kumar
, p. 9287 - 9293 (2016/10/13)
A stereoselective approach for the synthesis of haliclamide 1, a marine natural product, has been developed. The notable features of our synthesis include MacMillan cross aldol, Mitsunobu inversion, Yamaguchi-Hirao alkylation, Steglich esterification and
Regioselective Alkyl and Alkynyl Substitution Reactions of Epoxy Alcohols by the Use of Organoaluminum Ate Complexes: Regiochemical Reversal of Nucleophilic Substitution Reactions
Sasaki, Minoru,Tanino, Keiji,Miyashita, Masaaki
, p. 1765 - 1767 (2007/10/03)
(matrix presented) Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl- and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exa
Synthesis of (+)-Homononactic Acid via Iodoetherification
Kiyota, Hiromasa,Abe, Masaki,Ono, Yukie,Oritani, Takayuki
, p. 1093 - 1095 (2007/10/03)
(+)-Homononactic acid, one of the monomers of polynactin, and its 8-epimer were synthesized. The key step was cis-selective iodoetherification of the enone or the α-silyloxyolefin intermediates constructed with Wittig-Horner or Julia coupling reactions, r
Synthetic studies on tautomycin synthesis of segment B
Tsuboi, Katsunori,Ichikawa, Yoshiyasu,Naganawa, Atsushi,Isobe, Minoru,Ubukata, Makoto,Isono, Kiyoshi
, p. 5083 - 5102 (2007/10/03)
The synthesis of Segment B corresponding to the C26-C17 portion of tautomycin was accomplished by coupling reaction between the epoxide (Sub-segment B-l) and the dithiane (Subsegment B-2). The degradation product of tautomycin corresponding to the C26-C19 portion was also synthesized from Sub-segment B-1.
A Formal Synthesis of Aplysiatoxin: Enantioselective Synthesis of Kishi's Aldehyde
Okamura, Hiroaki,Kuroda, Satoru,Ikegami, Satoru,Tomita, Kenji,Sugimoto, Yu-ichi,et al.
, p. 10531 - 10554 (2007/10/02)
This paper describes the enantioselective synthesis of key fragments (12,18,24, and 35) for the synthesis of aplysiatoxin (1a), a potent cancer promoter, and their convergent assembly to Kishi's aldehyde (2).Since 2 has already been transformed into 1a in
Stereoselective Synthesis of erythro-Serricornin, (4R,6R,7S)-, and (4S,6R,7S)-4,6-Dimethyl-7-hydroxynonan-3-one, Stereoisomers of the Sex Pheromone of Cigarette Beetle
Chuman, Tatsuji,Kohno, Masahiro,Kato, Kunio,Noguchi, Masao,Nomi, Hiroko,Mori, Kenji
, p. 2019 - 2024 (2007/10/02)
A stereoselective synthesis of erythro-serricornin was completed starting from L-(+)-tartaric acid.The relative configuration of C(6)-methyl and C(7)-hydroxyl groups in naturally occurring serricornin was threo.
