Synthetic study on nikkomycins using addition reactions of nitrones
硝酮加成反应合成尼可霉素的研究
基本信息
- 批准号:11672122
- 负责人:
- 金额:$ 1.79万
- 依托单位:
- 依托单位国家:日本
- 项目类别:Grant-in-Aid for Scientific Research (C)
- 财政年份:1999
- 资助国家:日本
- 起止时间:1999 至 2001
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
Nikkomycin Bz, a dipeptide antibiotic, posseses γ-hydroxy-α-amino acid as the N-terminal amino acid and a nucleoside amino acid as the C-terminal amino acid.1) α-Allyloxycarbonylnitrone having a sugar auxiliary was explored. Using this method, the N-terminal amino acid moiety was synthesized.2) (5R) [and (5S)]-5,6-Dihydro-5-phenyl-2H-1, 4-oxazin-2-one N-oxides were designed and synthesized as the chiral (E)-geometry-fixed α-alkoxycarbonylrtitrones. The key intermediate of carbocy polyoxin C, the carbocyclic analogue of the C-terminal amino acid, was synthesized by employing 1,3-dipolar cycloaddition of the cyclic nitrone.3) Nucleophilic addition reaction of 2-trimethylsilyloxyfurah to N-Gulosyi-C-alkoxymetnyl-nitrones was explored. The key intermediate of polyoxin C, the C-terminai amino acid of nikkomycin Bz, was synthesized by employing this method.4) Methods mentioned above were applied to the synthesis of highly functionalized anti- and syn-β-substituted α-amino acids.5) Highly stereoselective cycloaddition of (5S)-5,6-dihydro-5-phenyl-2H-1 ,4-oxazin-2-one N-oxide with allyll alcohol in the presence of MgBr_2 was applied to the synthesis of an antibiotic clavalanine.
Nikkomycin Bz是一种二肽抗生素,其N末端氨基酸为γ-羟基-α-氨基酸,C末端氨基酸为核苷氨基酸。1)使用其探索了具有糖辅助剂的α-烯丙氧基羰基硝酮。方法,合成了N-末端氨基酸部分。2) (5R) [和(5S)]-5,6-二氢-5-苯基-2H-1, 4-恶嗪-2-酮N-氧化物被设计和合成为手性(E)-几何固定的α-烷氧基羰基滴酮的关键中间体。碳环多氧菌素 C(C 端氨基酸的碳环类似物)是通过使用 1,3-偶极环加成合成的3)探索了2-三甲基硅氧基呋喃与N-古洛基-C-烷氧基甲甲基硝酮的亲核加成反应,利用该方法合成了多抗素C的关键中间体,即尼可霉素Bz的C端氨基酸。 ) 上述方法应用于合成高功能化的反-和顺-β-取代α-氨基酸。5)在MgBr_2存在下,(5S)-5,6-二氢-5-苯基-2H-1,4-恶嗪-2-酮N-氧化物与烯丙醇进行高度立体选择性环加成反应,用于合成抗生素棒丙氨酸。
项目成果
期刊论文数量(14)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Osamu Tamura: "Design, Synthesis and 1,3-Dipolar Cycloaddition of (5R)[and (5S)]-5,6-Dihydro-5-phenyl-2H-1,4-oxazin-2-one N-Oxides as Chiral(E)-Geometry Fixed α-Alkoxycarbonylnitrones"J.Org.Chem.. 65・25. 8544-8551 (2000)
Osamu Tamura:“(5R)[和 (5S)]-5,6-二氢-5-苯基-2H-1,4-恶嗪-2-酮 N-氧化物的设计、合成和 1,3-偶极环加成手性(E)-几何固定的α-烷氧基羰基硝酮”J.Org.Chem.. 65・25. 8544-8551 (2000)
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O.Tamura, S.Yoshida, H.Sugita, N.Mita, Y.Uyama, N.Morita, M.Ishigur, T.Kawasaki, H.Ishibashi, M.Sakamoto: "Stereo-controlled Synthesis of Multi-functionallized β-Substituted α-amino acids : Nitrone cycloaddition Approach"Synlett. 1553-1556 (2000)
O.Tamura、S.Yoshida、H.Sugita、N.Mita、Y.Uyama、N.Morita、M.Ishigur、T.Kawasaki、H.Ishibashi、M.Sakamoto:“多功能β的立体控制合成-取代的α-氨基酸:硝酮环加成方法”Synlett. 1553-1556 (2000)
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O. Tamura, N. Mita, T. Okabe, T. Yamaguchi, C. Fukushima, M. Yamashita, Y. Morita, N. Morita, H. Ishibashi, M. Sakamoto: "Tandem transesterificaton and intramolecular cycloaddition of α-methoxycarbonylnitrones with chiral acyclic allyl alcohols : systemat
O. Tamura、N. Mita、T. Okabe、T. Yamaguchi、C. Fukushima、M. Yamashita、Y. Morita、N. Morita、H. Ishibashi、M. Sakamoto:“α-甲氧基羰基硝酮的串联酯交换和分子内环加成与手性无环烯丙醇:systemat
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O.Tamura, T.Kuroki, Y.Sakai, J.Takizawa, J.Yoshino, Y.Morita, N.Mita, K.Gotanda, M.Sakamoto: "Chelation Controlled 1,3-Dipolar Cycloaddition of 5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-Oxide with Allyl Alcohols : A Short-step Synthesis of Clavalanine Inter
O.Tamura、T.Kuroki、Y.Sakai、J.Takizawa、J.Yoshino、Y.Morita、N.Mita、K.Gotanda、M.Sakamoto:“螯合控制 5,6- 的 1,3-偶极环加成
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O.Tamura, T.Kuroki, Y.Sakai, J.Takizawa, J.Yoshino, Y.Morita, N.Mita, K.Gotanda, M.Sakamoto: "Chelation Controlled 1,3-Dipolar Cycloaddition of 5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-Oxide with Allyl Alcohols: A Short-step Synthesis of Clavalanine Interm
O.Tamura、T.Kuroki、Y.Sakai、J.Takizawa、J.Yoshino、Y.Morita、N.Mita、K.Gotanda、M.Sakamoto:“螯合控制 5,6- 的 1,3-偶极环加成
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TAMURA Osamu其他文献
TAMURA Osamu的其他文献
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{{ truncateString('TAMURA Osamu', 18)}}的其他基金
Development of reactions by means of novel activation of oximes
通过肟的新型活化反应的发展
- 批准号:
17K08221 - 财政年份:2017
- 资助金额:
$ 1.79万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
DEVELOPMENT OF NOVEL NITROGEN-CONTAINING 1,3-DIPOLARS
新型含氮1,3-偶极子的研制
- 批准号:
22590017 - 财政年份:2010
- 资助金额:
$ 1.79万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
CONSTRUCTION OF POLYCYCLIC SYSTEMS USING OXIDATION OF AROMATIC COMPOUNDS
利用芳香族化合物的氧化构建多环系统
- 批准号:
19590013 - 财政年份:2007
- 资助金额:
$ 1.79万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Documentary Studies on the French Constitution of 1795.
1795 年法国宪法的文献研究。
- 批准号:
18530026 - 财政年份:2006
- 资助金额:
$ 1.79万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Synthetk Studies on Multi Sorts of Biologically Active Cormpounds Using Nitrones Related to Amino Acids and Sugars
氨基酸和糖相关硝酮合成多种生物活性化合物的研究
- 批准号:
15590003 - 财政年份:2003
- 资助金额:
$ 1.79万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
The fundamental and clinical studies of proprioception of the ocular muscles.
眼肌本体感觉的基础和临床研究。
- 批准号:
63304049 - 财政年份:1988
- 资助金额:
$ 1.79万 - 项目类别:
Grant-in-Aid for Co-operative Research (A)
Study of the original and treatment of strabismus by EMG.
斜视的病因及治疗的肌电图研究。
- 批准号:
62480365 - 财政年份:1987
- 资助金额:
$ 1.79万 - 项目类别:
Grant-in-Aid for General Scientific Research (B)