- Stereoselective synthesis of novel ptilomycalin a analogs via successive 1,3-dipolar cycloaddition reactions and their Ca2+-ATPase inhibitory activity
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The pentacyclic guanidine compounds 4 and 5 were stereoselectively synthesized as novel ptilomycalin A and crambescidin analogs. The synthetic method involves successive 1,3-dipolar cycloaddition reactions which effectively access the key intermediates, t
- Georgieva, Angelina,Hirai, Manabu,Hashimoto, Yuichi,Nakata, Tadashi,Ohizumi, Yasushi,Nagasawa, Kazuo
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p. 1427 - 1432
(2007/10/03)
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- Selective synthesis of carbamate protected polyamines using alkyl phenyl carbonates
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Utilising alkyl phenyl carbonates, an economical, practical and versatile method for selective Boc, Cbz and Alloc protection of polyamines has been developed. This method allows Boc, Cbz and Alloc protection of primary amines in the presence of secondary amines by reaction of the polyamines with the alkyl phenyl carbonates. Also, this method allows mono carbamate protection of simple symmetrical aliphatic α,ω-alkanediamines in high yields with respect to the diamine. Finally, the method allows selective carbamate protection of a primary amine located on a primary carbon in the presence of a primary amine located on a secondary or a tertiary carbon in excellent yields.
- Pittelkow, Michael,Lewinsky, Rasmus,Christensen, Jorn Bolstad
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p. 2195 - 2202
(2007/10/03)
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- 49. Synthesis of tenuilobine, a bis-polyamine alkaloid from Oncinotis tenuiloba, and its transamidation to isotenuilobine
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From the leaves of Oncinotis tenuiloba STAPF, a novel polyamine alkaloid, tenuilobine (9), was isolated. This paper presents the synthesis of 9, as well as the base-catalyzed Zip reaction of 9, leading to the transamidation product isotenuilobine (10). Th
- Doll, Martin K.-H.,Guggisberg, Armin,Hesse, Manfred
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p. 541 - 547
(2007/10/03)
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- Synthesis of a Structural Analog of Ptilomycalin A
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Ptilomycalin A analog 2 was prepared by coupling amido alcohol 9 with guanidinium carboxylate 31.The synthesis of 2 requires 13 steps via a longest linear sequence from acrylate 22.
- Grillot, Anne-Laure,Hart, David J.
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p. 11377 - 11392
(2007/10/02)
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- Spermexatin and Spermexatol: New Synthetic Spermidine-Based Siderophore Analogues
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Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described.Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate.These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine.Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized.Thereagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine.The ability of these iron chelators to stimulate microbial growth is also described.
- Sharma, Sushil K.,Miller, Marvin J.,Payne, Shelley M.
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p. 357 - 367
(2007/10/02)
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- CONVENIENT ROUTES TO ALKYL-SUBSTITUTED POLYAMINES
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Alkyl-substituted polyamines, valuable for biological studies, can be prepared from N-phenylmethoxycarbonyl-1,4-diaminobutane (1b) and N-phenylmethoxycarbonyl-4-azidobutanamine (4a) by utilising the following reactions: (i) reduction of the phenylmethoxycarbonyl group to methyl by borane and (ii) combination of the Staudinger and aza-Wittig reactions .
- Golding, Bernard T.,O"Sullivan, Mary C.,Smith, Lewis L.
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p. 6651 - 6654
(2007/10/02)
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- Chemoselective Acylation of Primary Amines in the Presence of Secondary Amines with Acyl Cyanides. Highly Efficient Methods for the Synthesis of Spermidine and Spermine Alkaloid
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Acyl cyanides are highly useful reagents for the chemoselective acylation of primary amines in the presence of secondary amines.The reaction provides the versatile method for the shortstep synthesis of various naturally occurring polyamines.
- Murahashi, Shun-Ichi,Naota, Takeshi,Nakajima, Nobuyuki
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p. 879 - 882
(2007/10/02)
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- Total Synthesis of Parabactin, a Spermidine Siderophore
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The stereoselective total synthesis of parabactin (1) has been efficiently carried out using substituted 1,3-thiazolidine-2-thione as a leaving group.
- Nagao, Yoshimitsu,Miyasaka, Tadayo,Hagiwara, Yuichi,Fujita, Eiichi
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p. 183 - 187
(2007/10/02)
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