12-epi-vineomycinone B2 methyl ester | 89495-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 12-epi-vineomycinone B2 methyl ester
• 英文别名: methyl (3S)-4-[6-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl]-3-hydroxy-3-methylbutanoate
• CAS: 89495-28-3
• 化学式: C₂₆H₂₈O₁₀
• 分子量: 500.502
• InChiKey: TUWSZFDKMULJEZ-VTFNPOFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  170.82
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2-Chloro-5-methoxy-6-(prop-1-en-1-yl)naphthalene-1,4-dione 在 tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium sodium hydroxide 、 二甲基硫 、 dimethyl sulfide borane 、 双氧水 、 三溴化硼 、 potassium carbonate 、 臭氧 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 12-epi-vineomycinone B2 methyl ester
  参考文献：
  名称：

  葡萄霉素B2苷元的全合成

  摘要：

  Synthese du compose du titre qui est l'acide dihydroxy-1,5 [dihydroxy-4,5methyl-6 perhydropyrannyl-2]-6 β-hydroxy β-methyl anthraquinonebutyrique-2

  DOI：

  10.1021/ja00320a049

文献信息

• Convergent total synthesis of vineomycinone B2 methyl ester and its C(12)-epimer
  作者：Takashi Matsumoto、Miyoko Katsuki、Hideki Jona、Keisuke Suzuki

  DOI：10.1021/ja00018a041

  日期：1991.8

  Total syntheses of vineomycinone B2 methyl ester (7) and its C(12)-epimer (epi-7) have been completed. The key reaction for construction of the aryl C-glycoside linkage is the O --> C-glycoside rearrangement starting from D-olivosyl fluoride derivative 11 and anthrol derivative 21, which provides the regio- and stereocontrolled formation of the aryl C-glycoside sector of the target. The combination of Cp2HfCl2-AgClO4 serves as a particularly efficient promoter for this reaction. An extensive model study for attaching the side chain is presented. The Lochmann-Schlosser base cleanly effects ortho metalation of anthracene derivatives 19 and 20. The metalated species can be trapped as stannyl derivatives, from which the corresponding aryllithium species are generated by using n-BuLi or preferably MeLi in toluene. These specific reaction conditions are necessary to suppress the abnormal reaction of RLi reagents at the C(9)/C(10)-positions of the anthracenes. Coupling of the side chain moiety was efficiently carried out by such metalation of anthracene derivative 25 followed by reaction with chiral aldehyde (S)-29. The chiral aldehyde was derived from enantiomerically pure acid (S)-37 obtained by enzymatic kinetic resolution. Deoxygenation of the benzylic alcohol function followed by several steps allowed the total ynthesis of 7. Starting from (R)-aldehyde 29, the same sequence of reactions accomplished the total synthesis of epi-7. The epi series of intermediates provided firm evidence for the stereochemical homogeneity of synthetic 7.