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Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine Salacia prinoides
- G. Tanabe, Mika Sakano, T. Minematsu, Hisashi Matusda, M. Yoshikawa, O. Muraoka
- 20 October 2008
Abstract Synthesis and elucidation of absolute stereochemistry of salaprinol (3) isolated from the root and stems of Salacia prinoides, which has been used for the treatment of diabetes in India, Sri… Expand
Biological evaluation of 3'-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3' position in the side chain on the α-glucosidase inhibitory activity.
- G. Tanabe, T. Otani, +4 authors O. Muraoka
- Chemistry, Medicine
- Bioorganic & medicinal chemistry letters
- 15 May 2011
Four analogs with 3'-O-alkyl groups (9a: CH(3), 9b: C(2)H(5), 9c: C(13)H(27) or 9d: CH(2)Ph) instead of the 3'-O-sulfate anion in salacinol (1), a naturally occurring potent α-glucosidase inhibitor,… Expand
Syntheses and evaluation as glycosidase inhibitor of 1,5-dideoxy-1,5-imino-D-glucitol analogs of salacinol, a potent α-glucosidase inhibitor isolated from Ayurvedic medicine, Salacia reticulata
- G. Tanabe, Takanori Hatanaka, T. Minematsu, H. Matsuda, M. Yoshikawa, O. Muraoka
- 1 April 2009
- N-Alkylated deoxynojirimycin (10) bearing the same alkyl chain as salacinol (1), a potent α-glucosidase inhibitor isolated from Ayurvedic traditional medicine, Salacia reticulata, was found to… Expand
Chalcones as Synthetic Intermediates. A Facile Route to (±)-Magnosalicin, an Antiallergy Neolignan
A facile synthetic route was developed to (±)-magnosalicin (1), a new type of neolignan with antiallergy activity isolated from Magnolia salicifolia, starting from a chalcone, 1, 3-bis(2', 4',… Expand
Stereoselective total synthesis of acremomannolipin A and its anomer, the potent calcium signal modulators with a novel glycolipid structure: role of the stereochemistry at the anomeric center on the…
Abstract A full account of stereoselective total synthesis of a novel glycolipid, acremomannolipin A (1), the potent calcium signal modulator isolated from Acremonium strictum, by employing the… Expand
Synthesis of Azepines via a [6 + 1] Annulation of Ynenitriles with Reformatsky Reagents.
- Mitsuhiro Yoshimatsu, Miki Tanaka, +7 authors O. Muraoka
- Chemistry, Medicine
- The Journal of organic chemistry
- 16 September 2015
A protocol for the direct synthesis of azepines using a hafnium(III)-catalyzed [6 + 1] annulation of N-tethered ynenitriles with Reformatsky reagents is reported. A broad range of… Expand
Synthesis of 3-methyl- and 3,4-dimethylfurans using alkoxide, thiolate, and phenoxide-mediated cyclization of 4-oxahepta-1,6-diynes bearing sulfur and selenium functional groups
We have reported sodium alkoxide- or aryloxide-mediated cyclization of 4-oxahepta-1,6-diynes bearing the phenylsulfanyl group 1a–d. The reactions with diverse sodium alkoxides and aryloxide produced… Expand
ABSOLUTE STEREOSTRUCTURES OF PAEONISOTHUJONE, A NOVEL SKELETAL MONOTERPENE KETONE, AND DEOXYPAEONISUFFRONE, AND ISOPAEONISUFFRAL, TWO NEW MONOTERPENES, FROM MOUTAN CORTEX
Three new labile monoterpenes named paeonisothujone, deoxypaeonisuffrone, and isopaeonisuffral were isolated from Chinese Moutan Cortex, the root cortex of Paeonia suffruticosa ANDREWS. The absolute… Expand
Acylated iridoid glycosides with hyaluronidase inhibitory activity from the rhizomes of Picrorhiza kurroa Royle ex Benth.
Seven new acylated iridoid glycosides, picrorhizaosides A-G (1-7), were isolated from the methanol extract of the rhizomes of Picrorhiza kurroa Royle ex Benth. (Plantaginaceae), in addition to six… Expand
First total synthesis of crispine B by nitro aldol and the bischler-napieralski reaction
A pyrrolo[2,1-a]isoquinoline alkaloid, crispine B, was firstly synthesized in 55% overall yield from 3,4-dimethoxyaldehyde via five steps by employing nitro-aldol reaction and the… Expand