samaderine B | 158570-40-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: samaderine B
• 英文别名: samaderin B；(1R,4S,5R,8S,9R,10R,11S,12S,16S)-9,12-dihydroxy-4,11,15-trimethyl-3,7-dioxapentacyclo[8.8.0.01,5.04,8.011,16]octadec-14-ene-6,13,18-trione
• CAS: 158570-40-2
• 化学式: C₁₉H₂₂O₇
• 分子量: 362.379
• InChiKey: CVLVYBSPYHCGGU-VQXUUFQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1β,2β,5β,5aβ,7aα,11β,11aβ,11bα,14α)-1-hydroxy-1,7a,11a,11b-tetrahydro-11-methoxy-8,11a,14-trimethyl-2H-5a,5,2-(methanoxymetheno)naphth<1,2-d>oxepin-4,6,10(5H,7H,11H)-trione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以57%的产率得到samaderine B
  参考文献：
  名称：

  C19 Quassinoids: Total Synthesis of dL-Samaderin B

  摘要：

  The total synthesis of the novel C-19 quassinoid dl-samaderin B (2) is described. The synthesis commences with the known racemic pentacyclic ketone 6, which permits introduction of the C(11), C(12) trans diaxial arrangement of the hydroxyl groups in ring C. The synthesis features a copper(II)-mediated ring contraction of a delta-lactone (28) to a gamma-lactone (29). Subsequent elaboration of the ring A 1 beta-hydroxy-2-oxo-Delta(3,4) olefin unit, cleavage of the C(7), C(11) methoxymethyl ethers, selective oxidation at C(7), and deprotection of the C(1) hydroxyl affords samaderin B (2).

  DOI：

  10.1021/ja00096a018

文献信息

• C19 Quassinoids: Total Synthesis of dL-Samaderin B
  作者：Paul A. Grieco、Marta M. Pineiro-Nunez

  DOI：10.1021/ja00096a018

  日期：1994.8

  The total synthesis of the novel C-19 quassinoid dl-samaderin B (2) is described. The synthesis commences with the known racemic pentacyclic ketone 6, which permits introduction of the C(11), C(12) trans diaxial arrangement of the hydroxyl groups in ring C. The synthesis features a copper(II)-mediated ring contraction of a delta-lactone (28) to a gamma-lactone (29). Subsequent elaboration of the ring A 1 beta-hydroxy-2-oxo-Delta(3,4) olefin unit, cleavage of the C(7), C(11) methoxymethyl ethers, selective oxidation at C(7), and deprotection of the C(1) hydroxyl affords samaderin B (2).