Results 151 to 160 of about 1,931 (193)
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An enantiocontrolled synthesis of (−)-Swainsonine
Tetrahedron Letters, 1995Abstract (−)-Swainsonine 1 , first isolated from the fungus Rhizoctonia leguminicola , has been sythesized enantioseletively. The key step was the stereoselective iodoamination of trichloro- acetimidate derived from (Z)-olefinic allylic alcohol 7 .
Sung Ho Kang, Geun Tae Kim
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Detection of swainsonine-producing endophytes in Patagonian Astragalus species
Toxicon, 2019 Swainsonine has been identified as the toxin in legumes belonging to the genera Astragalus and Oxytropis throughout the world including China, North America, and South America.
Agustin Martinez +2 more
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The Journal of Organic Chemistry, 2002
The asymmetric synthesis of (-)-swainsonine via a nonchiral pool route that involves the Sharpless epoxidation to induce chirality is reported. The key steps involve vinyl epoxide aminolysis, ring-closing metathesis, and intramolecular N-alkylation to prepare the indolizidine ring and a highly diastereoselective cis-dihydroxylation using AD-mix-alpha ...
Karl B, Lindsay, Stephen G, Pyne
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The asymmetric synthesis of (-)-swainsonine via a nonchiral pool route that involves the Sharpless epoxidation to induce chirality is reported. The key steps involve vinyl epoxide aminolysis, ring-closing metathesis, and intramolecular N-alkylation to prepare the indolizidine ring and a highly diastereoselective cis-dihydroxylation using AD-mix-alpha ...
Karl B, Lindsay, Stephen G, Pyne
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Total syntheses of (+)-2,8,8a-tri-epi-swainsonine and (-)-1-epi-swainsonine
The Journal of Organic Chemistry, 1993Parallel syntheses of the title swainsonine-related enantiomers 9 and 15 were achieved in five steps and in 55% overall yield via enantiomeric threose N-benzylimines 4 and 10, derived from L- and D-tartaric acid, respectively. A stereospecific 4 + 4 homologative procedure using 2-(trimethylsiloxy)-furan (TMSOF), obtained from 2-furaldehyde, was ...
Giovanni Casiraghi +4 more
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Asymmetric total synthesis of (+)-swainsonine
Org. Biomol. Chem., 2011A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available l-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of α-sulfinyl carbanion as a key step. (+)-Swainsonine was obtained in 11.8% overall yield in 10 steps.
Soontorn, Chooprayoon +4 more
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Short step enantioselective synthesis of (−)‐swainsonine
Chirality, 2000Recent discovery of asymmetric desymmetrization of meso-heterocycles using (R,R)-(salen)manganese complex 2 as a catalyst allowed easy access to optically active 2,3,4-trisubstituted pyrrolidines. Taking advantage of this new reaction, we could achieve the short-step synthesis of (-)-swainsonine 1.
T, Punniyamurthy, R, Irie, T, Katsuki
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ChemInform Abstract: Stereoselective Synthesis of (+)‐Swainsonine and (‐)‐8,8a‐Di‐epi‐ swainsonine.
ChemInform, 1995AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
T. OISHI, T. IWAKUMA, M. HIRAMA, S. ITO
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Lysosomal hydrolases in macrophages exposed to swainsonine
Biochimica et Biophysica Acta (BBA) - Molecular Cell Research, 1983Swainsonine reversibly inhibits macrophage lysosomal acid alpha-mannosidase in vitro. When supplied to cultured cells for periods of up to 24 h, swainsonine penetrates the cells and produces a dose- and time-dependent inhibition of cellular alpha-mannosidase.
V A, Greenaway +3 more
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2000
Abstract Swainsonine is an indolizidine alkaloid best known for its occurrence in certain leguminous plants of Australia and the western United States (4). The offending plants are of ten grazed by livestock, and chronic ingestion has been linked to induction of neurological disease. In Australia, the culpable plant is the darling pea
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Abstract Swainsonine is an indolizidine alkaloid best known for its occurrence in certain leguminous plants of Australia and the western United States (4). The offending plants are of ten grazed by livestock, and chronic ingestion has been linked to induction of neurological disease. In Australia, the culpable plant is the darling pea
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Production of swainsonine by fungal endophytes of locoweed
Mycological Research, 2003Consumption of locoweeds, legumes endemic in arid western USA, has long been associated with locoism, a disease of ruminant animals. To explore the relationship between fungi associated with locoweed and locoweed toxicity, 11 locoweed populations from various sites in New Mexico were assessed for endophytic fungi.
Karen, Braun +3 more
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