SYNTHESIS OF (-) -SWAINSONINE AND OPTICALLY ACTIVE 3, 4-DIHYDROXY-2-HYDROXYMETHYLPYRROLIDINES
- 1 January 1987
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 35 (5) , 2140-2143
- https://doi.org/10.1248/cpb.35.2140
Abstract
(-)-Swainsonine, (2R,3S,4R)- and (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine (2 and 3) were synthesized stereo-selectively starting from (R)- and (S)-glutamic acid derivatives, respectively.This publication has 15 references indexed in Scilit:
- Synthesis of hydroxylated pyrrolidines derivatives as potential inhibitors of SAH/MTA nucleosidase.Tetrahedron Letters, 1987
- Potent competitive inhibition of α-galactosidase and α-glucosidase activity by 1,4-dideoxy-1,4-iminopentitols: syntheses of 1,4-dideoxy-1,4-imino-d-lyxitol and of both enantiomers of 1,4-dideoxy-1,4-iminoarabinitolTetrahedron Letters, 1985
- Enantioselective synthesis of swainsonine, a trihydroxylated indolizidine alkaloidThe Journal of Organic Chemistry, 1985
- SYNTHESIS OF TWO STEREOISOMERS OF SWAINSONINEChemistry Letters, 1985
- Studies of an immunomodulator, swainsonine. II. Effect of swainsonine on mouse immunodeficient system and experimental murine tumor.The Journal of Antibiotics, 1985
- Efficient syntheses of naturally occurring 3,4-dihydroxyprolines: Electrophile-mediated lactonization of 2-amino-3-hydroxy-4-pentenoic acid derivativesTetrahedron Letters, 1985
- TOTAL SYNTHESIS OF (−)-SWAINSONINE, AN α-MANNOSIDASE INHIBITOR ISOLATED FROM SWAINSONA CANESCENSChemistry Letters, 1984
- Synthetic Studies on Optically Active b-Lactams. Asymmetric Synthesis of b-Lactams by the Cyclocondensation Utilizing Chiral Heterocyclic Compounds Derived from L-(+)-Tartaric Acid and (S)-Glutamic AcidHETEROCYCLES, 1984
- Total synthesis of (-)-domoic acid. A revision of the original structureJournal of the American Chemical Society, 1982
- A Spectroscopic Investigation of Swainsonine: An α-Mannosidase Inhibitor Isolated from Swainsona canescensAustralian Journal of Chemistry, 1979