117901-01-6Relevant academic research and scientific papers
Stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol
Agostinelli, Sonia,De Angelis, Martina,Lucarini, Claudia,Primitivo, Ludovica,Ricelli, Alessandra,Righi, Giuliana,Sappino, Carla
, (2020)
The first stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol is described. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation (AD) of suitable optically active olefin, the chiral vin
A short convergent synthesis of the [3.2.1]dioxabicyclooctane subunit of sorangicin A via regioselective epoxide opening
Raghavan, Sadagopan,Nyalata, Satyanarayana
, p. 1071 - 1077 (2018)
In this paper, we disclose the synthesis of the dioxabicyclo[3.2.1]octane subunit of the potent antibiotic sorangicin A. The synthesis was achieved in a convergent manner in 8 steps. Regio- and stereoselective intermolecular epoxide opening, ring-closing metathesis and iodo-etherification are key steps. cis-2-Butene diol has been employed as a common staring material.
Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of 1,4-dideoxy-1,4-imino-D-galactitol and 1,4-dideoxy-1,4-imino-D-glucitol
Righi, Giuliana,Mandic', Emanuela,Sappino, Carla,Dema, Ergys,Bovicelli, Paolo
, p. 100 - 105 (2016)
Herein the total synthesis of the pyrrolidine alkaloids 1,4-dideoxy-1,4-imino-D-galactitol and its diastereoisomer 1,4-dideoxy-1,4-imino-D-glucitol is described, starting from a common optically active precursor. The key step in our approach was the doubl
Stereoselective total synthesis of multiplolide A and of a diastereoisomer
Reddy, Bandi Chennakesava,Bangade, Vikas Madhukar,Ramesh, Palakuri,Meshram, Harshadas Mitaram
, p. 266 - 274 (2013/03/28)
A stereoselective total synthesis of multiplolide A (1) and of its diastereoisomer 2 was described from easily accessible starting materials (Schemes 2-4). The synthetic strategy involves a Jacobsen resolution, Sharpless epoxidation, Swern oxidation, Yamaguchi reaction, and ring-closing metathesis (RCM). Copyright
Synthesis of all four stereoisomers of leucomalure, components of the female sex pheromone of the Satin moth, Leucoma salicis
Muto, Shin-etsu,Mori, Kenji
, p. 1300 - 1307 (2007/10/03)
Lipase PS-C (Amano)-catalyzed asymmetric acetylation of (±)-4-(tert-butyldiphenylsilyloxy)-cis-2,3-epoxy-1-butanol afforded the (2R,3S)-epoxy alcohol and the (2S,3R)-epoxyacetate, which were converted into all of the four stereoisomers of leucomalure [(3Z
γ-allyl Phosphinoyl Phenyl Sulfone (GAPPS): A Conjunctive Reagent for the Synthesis of EE, EZ, and ET 1,3-Dienes
Li, Xiaojin,Lantrip, Douglas,Fuchs, Philip L.
, p. 14262 - 14263 (2007/10/03)
A three-operation conjunctive strategy is available for the synthesis of EE, EZ, and ET dienes. This protocol employs a sequential Wadsworth?Emmons reaction using a GAPPS reagent followed by alkylation of an allylic sulfone anion, and finally ligand-mediated, palladium-catalyzed desulfonylation. Copyright
Diastereoface differentiation in addition of lithium enolates to chiral α, β-epoxyaldehydes
Escudier, Jean-Marc,Baltas, Michel,Gorrichon, Liliane
, p. 5253 - 5266 (2007/10/02)
The aldolisation reaction of lithium ester enolates with chiral α,β-epoxyaldehydes 2a-2f has been investigated. The reaction proceeds with diastereofacial preference in favour of the anti isomer (anti: syn ≈ 4:1) and can be greatly enhanced in the case of
APPLICATION OF BIOCHEMICAL METHODS IN ENANTIOSELECTIVE SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS
Mori, Kenji
, p. 393 - 406 (2007/10/02)
Enzymes as well as yeasts were used in enantioselective syntheses of bioregulators such as hormones and semiochemicals.Lipases and esterases were employed in achieving optical resolution, conversion of meso-compounds to optically active compounds, and macrolactonization.Lactase effected glucosidation of a phenolic hydroxy ketone without any protection of the functional groups.Yeasts provided a variety of optically active hydroxy esters and ketones, which served as versatile non-racemic chiral building blocks.
A NEW ENANTIO AND DIASTEREOSELECTIVE SYNTHESIS OF 2-AZETIDINONES AS USEFUL INTERMEDIATES OF β-LACTAM ANTIBIOTICS
Bonini, Carlo,Fabio, Romano Di
, p. 815 - 818 (2007/10/02)
An expeditious enantio and diastereoselective route to β-lactam synthons has been developed; two novel key radical reactions allowed us to obtain two useful intermediates in the synthesis of thienamycin and PS-5.
