(+)-crassalactone B | 918907-24-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (+)-crassalactone B
• 英文别名: [(2R,3S,3aS,6aR)-2-[(R)-hydroxy(phenyl)methyl]-5-oxo-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-3-yl] (E)-3-phenylprop-2-enoate
• CAS: 918907-24-1
• 化学式: C₂₂H₂₀O₆
• 分子量: 380.397
• InChiKey: FHGDRFDHIZAQKE-PENPKOISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3S,3aS,6aR)-2-((R)-benzyloxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl cinnamate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(+)-crassalactone B
  参考文献：
  名称：

  Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone

  摘要：

  The total synthesis of (+)-crassalactone B (+)-crassalactone C (+)-howiionol A (+)-tricinnamate (+)-goniofufurone and (+)-dicinnamoyl goniofufurone is achieved by a chit-on approach starting from diacetone D-glucose (DAG) Mitsunobu inversion Wittig olefination and ring closing metatheses were used as key steps for (+)-howiionol A and (+)-tricinnamate Meldrum s acid was used for the synthesis of (+)-crassalactone C (+)-goniofufurone and (+)-dicinnamoyl goniofufurone Yamaguchi esterification was used for (+)-crassalactone B while a Grignard reaction followed by concomitant deallylation was first reported in the synthesis of (+)-dicinnamoyl goniofufurone (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.016

文献信息

• Design, synthesis and SAR analysis of antitumour styryl lactones related to (+)-crassalactones B and C
  作者：Goran Benedeković、Mirjana Popsavin、Jovana Francuz、Ivana Kovačević、Vesna Kojić、Gordana Bogdanović、Vladimir Divjaković、Velimir Popsavin

  DOI：10.1016/j.ejmech.2014.09.064

  日期：2014.11

  A series of styryl lactones containing the cinnamic acid ester groups such as (+)-crassalactones B (3a) and C (4a), 5,7-di-O-cinamoyl derivative 6, the corresponding 7-epimers and 7-deoxy derivatives have been synthesized, characterized and evaluated for their in vitro antitumour activity against a panel of several human tumour cell lines. Twelve new analogues such as 5-O- or 7-O-(4-methoxycinnamoyl)

  一系列含有肉桂酸酯基的苯乙烯基内酯，如（+）-crassalactones B（3a）和C（4a），5,7- di - O - cinamoyl衍生物6，相应的7-epimers和7-deoxy衍生物已经合成，表征和评估了它们对一组人肿瘤细胞系的体外抗肿瘤活性。十二个新的类似物，例如5- O-或7 - O-（4-甲氧基肉桂酰基），5- O-或7 - O-（4-硝基肉桂酰基）和5- O-或7 - O-（4-氟肉桂酰基）酯goniofufurone（ - （+）的图3b - d），7-外延在SAR研究中，已经准备好使用-（+）-goniofufurone（epi - 3b - d）以及7-脱氧衍生物5b - d来关联所有化合物。一些类似物对选定的人类肿瘤细胞系显示出强大的抗增殖作用，但没有一个对正常胎儿肺成纤维细胞（MRC-5）具有细胞毒性。因此，发现7- epi- crassalactone
• Divergent total synthesis of crassalactones B and C and evaluation of their antiproliferative activity
  作者：Goran Benedeković、Ivana Kovačević、Mirjana Popsavin、Jovana Francuz、Vesna Kojić、Gordana Bogdanović、Velimir Popsavin

  DOI：10.1016/j.tet.2015.05.040

  日期：2015.7

  diacetone d-glucose (4) as a chiral precursor. The key steps of the synthesis of both targets 2 and 3 were a stereo-selective addition of phenyl magnesium bromide to a dialdose derivative, a regioselective introduction of the cinnamic acid residue, and a stereospecific furano-lactone ring formation by cyclocondensation of a suitable hemiacetal derivative with Meldrum's acid. No protection is necessary

  通过利用双丙酮d-葡萄糖（4）作为手性前体，实现了细胞毒性天然产物（+）-内酯B（2）和C（3）的不同总合成。合成靶标2和3的关键步骤是将苯基溴化镁立体选择性地添加到二糖衍生物中，肉桂酸残基的区域选择性引入以及通过合适的半缩醛的环缩形成立体特异性的呋喃内酯环。麦德鲁姆酸的衍生物。合成（+）-crassalactone C（3不需要保护），除了在商业上可获得的起始原料4中已经存在的双丙酮化物功能。由相同的起始原料制备（+）-克拉内酯B（2），需要在整个合成过程中使用单个甲硅烷基醚保护基。评价合成的天然产物对PC3，HT29和A549人肿瘤细胞系的体外抗增殖活性。
• Divergent synthesis of cytotoxic styryl lactones isolated from Polyalthia crassa. The first total synthesis of crassalactone B
  作者：Velimir Popsavin、Goran Benedeković、Mirjana Popsavin、Vesna Kojić、Gordana Bogdanović

  DOI：10.1016/j.tetlet.2010.04.114

  日期：2010.6

  The first total synthesis of (+)-crassalactone B (2) and a new syntheses of (+)-crassalactone C (3) has been achieved starting from d-glucose. The natural products 2 and 3 can be selectively accessed by changing the conditions for TBDPS cleavage in the final intermediate 16. The synthesized natural products were evaluated for their cytotoxic activity against a panel of human tumour cell lines.

  从d-葡萄糖开始，首次合成了（+）-B内酯B（2）和新的（+）cr内酯C（3）。通过改变最终中间体16中TBDPS裂解的条件，可以选择性地获得天然产物2和3。评价合成的天然产物对一组人类肿瘤细胞系的细胞毒性活性。
• Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone
  作者：Gangavaram V.M. Sharma、Samala Mallesham

  DOI：10.1016/j.tetasy.2010.10.016

  日期：2010.11

  The total synthesis of (+)-crassalactone B (+)-crassalactone C (+)-howiionol A (+)-tricinnamate (+)-goniofufurone and (+)-dicinnamoyl goniofufurone is achieved by a chit-on approach starting from diacetone D-glucose (DAG) Mitsunobu inversion Wittig olefination and ring closing metatheses were used as key steps for (+)-howiionol A and (+)-tricinnamate Meldrum s acid was used for the synthesis of (+)-crassalactone C (+)-goniofufurone and (+)-dicinnamoyl goniofufurone Yamaguchi esterification was used for (+)-crassalactone B while a Grignard reaction followed by concomitant deallylation was first reported in the synthesis of (+)-dicinnamoyl goniofufurone (C) 2010 Elsevier Ltd All rights reserved