79831-76-8Relevant articles and documents
An efficient, highly stereoselective synthesis of (+)-castanospermine
Anzeveno, Peter B.,Angell, Paul T.,Creemer, Laura J.,Whalon, Michael R.
, p. 4321 - 4324 (1990)
An efficient, highly stereoselective synthesis of (+)-castanospermine (1) has been achieved from 1,2-0-isopropylidene-α-Dglucofuranurono-6,3-lactone (2).
The chemistry of castanospermine, part III: e, an unusual route to a novel compound
Furneaux,Mason,Tyler
, p. 3055 - 3058 (1995)
Castanospermine-6-phosphate (6) is formed efficiently from 6-chloro-6-deoxycastanospermine (2) by an unusual nucleophilic displacement of chloride by a (di)hydrogenorthophosphate anion.
Stereoselective Total Syntheses of (+)-Castanospermine and Neu5Ac Methyl Ester
Myeong, In-Soo,Lee, Yong-Taek,Kang, Jihun,Ham, Won-Hun
, p. 4211 - 4220 (2019/04/30)
Concise and stereocontrolled total syntheses of (+)-castanospermine and N-acetylneuraminic acid methyl ester were achieved from diastereomerically enriched anti,syn,syn-1,3-oxazine and anti,syn,anti-1,3-oxazine, respectively. The key step in this strategy was the stereoselective BF3·OEt2-mediated allylation.
Diastereoselective nitrenium ion-mediated cyclofunctionalization: Total synthesis of (+)-castanospermine
Bowen, Edward G.,Wardrop, Duncan J.
supporting information; experimental part, p. 5330 - 5333 (2011/02/21)
The asymmetric total synthesis of the α-glucosidase inhibitor (+)-castanospermine is reported. The central theme in our approach to this polyhydroxylated alkaloid is the simultaneous generation of the piperidine ring and the C-1/8a erythro stereodiad thro
A flexible approach to azasugars: asymmetric total syntheses of (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and (+)-1-epi- castanospermine
Liu, Gang,Wu, Tian-Jun,Ruan, Yuan-Ping,Huang, Pei-Qiang
experimental part, p. 5755 - 5768 (2010/08/19)
The asymmetric total synthesis of natural azasugars (+)-castanospermine, (+)-7-deoxy-6-epI-castanospermine, and synthetic (+)-1-epi-castanospermine has been accomplished in nine to ten steps from a common chiral building block (S)-8. The method features a powerful chiral relay strategy consisting of a highly diastereoselective vinylogous Mukaiyama-type reaction with either chiral or achiral aldehydes (≥ 95% de; de = diastereomeric excess) and a diastereodivergent reduction of tetramic acids, which allows formation of three continuous stereogenic centers with high diastereo-selectivities. The method also provides a flexible access to structural arrays of 5-(α-hydroxyalkyl) tetramic acids, such as 17/34, and 5-(α-hydroxyalkyl)-4-hydroxyl-2- pyrrolidinones, such as 18 and 25/35 a. The method constitutes the first realization of the challenging chiral synthons A and D and thus of the conceptually attractive retrosynthetic analysis shown in Scheme 1 in a highly enantioselective manner.
A concise synthesis of castanospermine by the use of a transannular cyclization
Jensen, Thomas,Mikkelsen, Mette,Lauritsen, Anne,Andresen, Thomas L.,Gotfredsen, Charlotte H.,Madsen, Robert
experimental part, p. 8886 - 8889 (2010/03/01)
(Chemical Equation Presented) A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl α-D- glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyr
Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation
Ceccon, Julien,Danoun, Gregory,Greene, Andrew E.,Poisson, Jean-Franois
scheme or table, p. 2029 - 2031 (2009/09/04)
An asymmetric synthesis of (+)-castanospermine is presented in which enol ether metathesis-hydroboration/oxidation is used for stereoselective installation of the trans-trans hydroxyl groups on the piperidine ring of the alkaloid.
Synthesis of castanospermine
Machan, Theeraphan,Davis, Andrew S.,Liawruangrath, Boonsom,Pyne, Stephen G.
, p. 2725 - 2732 (2008/09/19)
The diastereoselective synthesis of castanospermine is described in 11 synthetic steps from l-xylose. The borono-Mannich reaction between l-xylose, allylamine, and (E)-styrene boronic acid gives a tetrahydroxy amine with the desired configurations for C-6
Intramolecular 5-endo-trig aminomercuration of β-hydroxy-γ- alkenylamines: Efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues
Karanjule, Narayan S.,Markad, Shankar D.,Shinde, Vaishali S.,Dhavale, Dilip D.
, p. 4667 - 4670 (2007/10/03)
The intramolecular aminomercuration reaction of sugar-derived β-hydroxy-γ-alkenylamines 8a-c undergoes 5-endo-trig cyclization in high yield. The sugar-substituted pyrrolidines thus obtained were elaborated to the synthesis of polyhydroxylated indolizidin
A concise sequential photochemical-metathesis approach for the synthesis of (+)-castanospermine and possible uniflorine-A stereoisomers
Zhao, Zhiming,Song, Ling,Mariano, Patrick S.
, p. 8888 - 8894 (2007/10/03)
A recently developed strategy for polyhydroxylated indolizidine ring construction has been applied to the synthesis of (+)-castanospermine and possible isomers of uniflorine-A. The routes to these targets rely on the use of the earlier discovered photocyclization reaction of pyridinium perchlorate in a concise route for preparation of a key N-allylacetamidocyclopentendiol intermediate. Ring rearrangement metathesis of this substance gives an allyl-tetrahydropyridine, which is then transformed to the targets by execution of regio- and stereo-controlled hydroxylation processes followed by indolizidine ring construction.
