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Advances in the Chemistry of (−)‐D‐Swainsonine

ChemistrySelect, 2022
Abstract (−)‐D‐Swainsonine is an indolizidine alkaloid molecule with a fused piperidine and pyrrolidine ring system. It has been the first glycoprotein‐processing inhibitor to be selected for clinical testing as an anticancer drug.
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Swainsonine: a new antineoplastic immunomodulator.

Journal of the National Medical Association, 1989
Swainsonine, an indolizidine alkaloid with immunomodulatory activity, has been found to be effective in inhibiting metastatic dissemination and growth of primary tumors of both murine and human origins. The unique ability of swainsonine to exhibit antimetastatic, anti-proliferative, and immunomodulatory activity imparts this drug a promising future in ...
Mohla, S   +7 more
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Water deficit induces swainsonine of some locoweed taxa, but with no swainsonine-growth trade-off

Acta Oecologica, 2012
Environmental factors like nutrient availability (e.g., C:N) and water deficit can influence secondary metabolites levels in plants and fungal endophytes. Locoweeds (Astragalus and Oxytropis spp.) contain swainsonine (SWA), an alkaloid that causes chronic vertebrate toxicity.
Amber D. Vallotton   +3 more
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Divergent syntheses of stereoisomers of swainsonine: (−)-8-epi-, (−)-8a-epi- and (−)-8,8a-diepi-swainsonine

Tetrahedron Letters, 1989
Abstract Divergent stereoselective syntheses of three stereoisomers 2–4 of swainsonine (1) starting from the readily available common intermediates 5a,b are described. A moderate to good stereoselectivity has been achieved by an allylic oxygen substituent.
Young Gyu Kim, Jin K. Cha
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Total Synthesis of (-)-Swainsonine

1997
Abstract Discussion Points Explain the selectivity of the hetero Diels–Alder reaction of step I and suggest a reason for the lower selectivity (endo:exo 1.3:1) observed when the reaction was run in chloroform. Explain the selectivity observed in the osmylation step o.
M Naruse, S Aoyagi, C Kibayashi,
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Recent Developments on the Synthesis of (-)-Swainsonine and Analogues

Current Organic Synthesis, 2005
AbstractFor Abstract see ChemInform Abstract in Full Text.
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Crystal structure of swainsonine diacetate

Australian Journal of Chemistry, 1980
The crystal structure of swainsonine diacetate, C12H19NO5, has been determined at 295(1) K by single-crystal X-ray diffraction and refined by least squares to a residual of 0.054 for 521 'observed' reflections. Crystals are orthorhombic, P212121, a 18.783(9), b 13.497(6), c 5.164(3) ?, Z 4.
BW Skelton, AH White
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Custer, selenium and swainsonine.

Veterinary and human toxicology, 2001
The Battle of Little Bighorn was fought over 100 y ago but many controversies remain. Some feel the defeat of Custer could have been avoided if Benteen and Reno had united with Custer. A slow-moving pack train may have hindered the troops of Benteen and Reno from joining up with Custer.
H F, Hintz, L J, Thompson
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A Practical Synthesis of (−)-Swainsonine

The Journal of Organic Chemistry, 1996
William H., Pearson, Erik J., Hembre
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Synthesis of (-)-Swainsonine

Synfacts, 2007
S. Pyne, C. Au
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