125279-72-3Relevant articles and documents
New concise total synthesis of (+)-lentiginosine and some structural analogues
Cardona, Francesca,Moreno, Guillermo,Guarna, Francesco,Vogel, Pierre,Schuetz, Catherine,Merino, Pedro,Goti, Andrea
, p. 6552 - 6555 (2005)
An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.
Structure-guided engineering of D-fructose-6-phosphate aldolase for improved acceptor tolerance in biocatalytic aldol additions
Soler, Anna,Gutiérrez, Mariana L.,Bujons, Jordi,Parella, Teodor,Minguillon, Cristina,Joglar, Jesús,Clapés, Pere
, p. 1787 - 1807 (2015)
Abstract A structure-guided redesign of D-fructose-6-phosphate aldolase from Escherichia coli (FSA) was devised for improving the acceptor tolerance towards α-substituted and conformationally constrained aldehydes. FSA A129S/R134X/A165G/S166G and L107Y/A1
Total syntheses of (±)-lentiginosine and (±)-1-epi-lentiginosine from hexahydro-1H-indol-3-one
Sha, Chin-Kang,Chau, Chi-Min
, p. 499 - 501 (2003)
Total syntheses of (±)-lentiginosine 1 and (±)-1-epi-lentiginosine 2 were achieved efficiently from hexahydro-1H-indol-3-one 7.
Enhanced trans diastereoselection in the allylation of cyclic chiral N-acyliminium ions. Synthesis of hydroxylated indolizidines
Klitzke, Clécio Fernando,Pilli, Ronaldo Aloise
, p. 5605 - 5608 (2001)
A short synthesis of hydroxylated indolizidines is reported. The key steps were the allylation of chiral cyclic N-acyliminium ions derived from malic and tartaric acids, followed by ring-closing metathesis.
A novel concise total synthesis of (+)-lentiginosine
Feng, Zhi-Xiang,Zhou, Wei-Shan
, p. 497 - 498 (2003)
A total synthesis of (+)-lentiginosine was achieved by using ethyl 3-(pyridin-2-yl)acrylate N-oxide as the starting material and an improved Sharpless asymmetric dihydroxylation as the key step.
Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate
Prasad, Kavirayani R.,Rangari, Vipin Ashok
, (2019/08/20)
A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant sulfinamides formed in the reaction. The formed products serve as excellent building blocks for the synthesis of natural products. This has been demonstrated in the collective total synthesis of lentiginosine, (+)-α-conhydrine and methyldihydropalustramate.
Redox-Neutral α-C-H Functionalization of Pyrrolidin-3-ol
Yi, Cheng-Bo,She, Zhi-Ying,Cheng, Yong-Feng,Qu, Jin
, p. 668 - 671 (2018/02/09)
A redox-neutral α-C-H oxygenation of commercially available pyrrolidin-3-ol with a monoprotected p-quinone generated an N-aryliminium ion intermediate, which reacted in situ with boronic acid nucleophiles to produce a series of cis-2-substituted pyrrolidin-3-ols. With this strategy, 8-epi-(-)-lentiginosine was synthesized from (3R,4R)-pyrrolidine-3,4-diol in three steps.