138323-07-6Relevant articles and documents
Total synthesis of padanamides A and B
Long, Bohua,Tang, Shoubin,Chen, Ligong,Qu, Shiwei,Chen, Bo,Liu, Junyang,Maguire, Anita R.,Wang, Zhuo,Liu, Yuqing,Zhang, Hui,Xu, Zhengshuang,Ye, Tao
supporting information, p. 2977 - 2979 (2013/05/22)
The first total syntheses of padanamides A and B have been achieved, unambiguously confirming their structures. The Royal Society of Chemistry.
Macrolide analogues of the novel immunosuppressant sanglifehrin: New application of the ring-closing metathesis reaction
Martin Cabrejas, Luisa M.,Rohrbach, Stefan,Wagner, Dieter,Kallen, Joerg,Zenke, Gerhard,Wagner, Juergen
, p. 2443 - 2446 (2007/10/03)
Macrocycles containing a conjugated 1,3-diene moiety have been synthesized for the first time in good yields by the ring-closing metathesis reaction [Eq. (1)]. The new compounds represent cyclophilin-binding, simplified analogues of the macrocyclic core of sanglifehrin A, an immunosuppressant which binds with high affinity to cyclophilin.
Asymmetric synthesis of (3S)-2,3,4,5-tetrahydropyridazine-3-carboxylic acid and its methyl ester 1
Aspinall, Ian H.,Cowley, Phillip M.,Mitchell, Glynn,Rajnor, Clive M.,Stoodley, Richard J.
, p. 2591 - 2599 (2007/10/03)
Methyl (2E,4E′)-5-(2′,3′,4′,6′-tetra-O-acetyl-p-D- glucopyranosyloxy)penta-2,4-dienoate 16a, assembled by a Wittig condensation of tributyl(methoxycarbonylmethylene)phosphorane 19a and (2E)-3-(2′,3′,4′,6′-tetra-O-acetyl-′- Dglucopyranosyloxy)propenal 20, displays excellent Re-face reactivity towards diethyl azodicarboxylate 15a, bis(2,2,2trichloroethyl) azodicarboxylate 15b, dibenzyl azodicarboxylate 15c, diisopropyl azodicarboxylate 15d and di-tertbutyl azodicarboxylate 15e in thermal hetero-Diels-Alder reactions to give the cycloadducts 17a-e. When subjected to the action of hydrogen over palladium-carbon, the cycloadducts 17a, 17b, 17d and 17e undergo hydrogenation of their olefinic bonds to give the dihydro derivatives 18a, 18b, 18d and 18e; in the case of the cycloadduct 17c, hydrogenolysis of the benzyloxycarbonyl group also occurs to give methyl (35)-2,3,4,5-tetrahydropyridazine-3carboxylate Ib with an ee of 98% and 2,3,4,6-tetra-O-acetyl-′-D-glucopyranose 22. Compound Ib, with an ee of 98%, is also available from the dihydro derivative 18e by the action of trifluoroacetic acid; however, under the acidic conditions, a condensation reaction between the aglycone Ib and the glycone 22 competes to give methyl (35)-2,3,4,5tetrahydro-2-(2′,3′,4′,6′-tetra-0-acetyl- ′-D-glucopyranosyl)pyridazine-3-carboxylate25. Sodium (35)-2,3,4,5-tetrahydropyridazine-3-carboxylate le, with an ee of 99%, is available from the ester Ib by a saponification reaction. The trifluoroacetic acid salt 27, with an ee of 95%, is obtained from benzyl (35,6S)1,2-bis(tert-butoxycarbonyl)-1,2,3,6-tetrahydro-6-(2′,3′, 4′,6′-tetra-O-acetyl-β-D-glucopyranosyIoxy)pyridazine-3- carboxylate 17g by a hydrogenation-trifluoroacetolysis sequence. A hetero-Diels-Alder reaction involving the benzyl pentadienoate 16c and di-tert-butyl azodicarboxylate 15e provides the cycloadduct 17g. The Royal Society of Chemistry 1999.
Dehydrooligopeptides. XVI. Convenient syntheses of two kinds of antrimycins Av and Dv containing dehydrovaline residues
Nakamura,Ito,Shin
, p. 2151 - 2161 (2007/10/02)
Eight kinds of peptide antibiotics, antrimycins (1), consist of four sorts of unusual α-amino acids, that is, hydroxymethylserine, (2S,3S)-2,3-diaminobutanoic acid, (S)-2,3,4,5-tetrahydro-3-pyridazinecarboxylic acid, and dehydrovaline (ΔVal) or (E)-dehydr
Useful Syntheses of (3S)-2,3,4,5-Tetrahydropyridazine-3-carboxylic Acid and Its Dehydrotetrapeptide Derivatives
Nakamura, Yutaka,Shin, Chung-gi
, p. 1953 - 1956 (2007/10/02)
The stereoselective synthesis of (3S)-2,3,4,5-tetrahydropyridazine-3-carboxylic acid (Pya), which is a cyclic α-amino acid at center of antrimycins (1), was successful.Moreover, the synthesis of the C-terminal dehydrotetrapeptide of 1 containing Pya residue at N-terminus is described.
