6-epi-casuarine | 260247-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: 6-epi-casuarine
• 英文别名: (1R,2R,3R,6R,7S,8R)-3-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,2,6,7-tetrol
• CAS: 260247-75-4
• 化学式: C₈H₁₅NO₅
• 分子量: 205.211
• InChiKey: AXTGOJVKRHFYBT-ORBTUSEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3R,4R,5R)-N-benzyloxycarbonyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(2-propenyl)pyrrolidine 在 盐酸 、 叔丁基过氧化氢 、 selenium(IV) oxide 、 四氧化锇 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 180.0h， 生成 6-epi-casuarine
  参考文献：
  名称：

  Stereocomplementary synthesis of casuarine and its 6-epi-, 7-epi-, and 6,7-diepi-stereoisomers

  摘要：

  立体互补策略可实现从环状亚硝基化合物和亚硝基化合物衍生的醛中高效合成卡苏林、6-epi-卡苏林、7-epi-卡苏林和6,7-二epi-卡苏林。它们的糖苷酶抑制剖面进行了比较。

  DOI：

  10.1039/d1ob01725j

文献信息

• Total Synthesis of Uniflorine A, Casuarine, Australine, 3-<i>epi</i>-Australine, and 3,7-Di-<i>epi</i>-australine from a Common Precursor
  作者：Thunwadee Ritthiwigrom、Anthony C. Willis、Stephen G. Pyne

  DOI：10.1021/jo902355p

  日期：2010.2.5

  A flexible method for the diastereoselective total synthesis of the pyrrolizidine alkaloids uniflorine A, casuarine, australine, and 3-epi-australine and the unnatural epimer 3,7-di-epi-australine from a common chiral 2,5-dihydropyrrole precursor is described.

  描述了一种灵活的方法，可从一种常见的手性2,5-二氢吡咯前体非对映选择性地合成吡咯烷核生物碱单花碱A，木麻黄，奥曲林和3- Epi- australine和非天然差向异构体3,7-di- epi - australine 。
• SmI₂-Mediated Radical Cross-Couplings of α-Hydroxylated Aza-hemiacetals and<i>N</i>,<i>S</i>-Acetals with α,β-Unsaturated Compounds: Asymmetric Synthesis of (+)-Hyacinthacine A₂, (−)-Uniflorine A, and (+)-7-<i>epi</i>-Casuarine
  作者：Xue-Kui Liu、Shi Qiu、Yong-Gang Xiang、Yuan-Ping Ruan、Xiao Zheng、Pei-Qiang Huang

  DOI：10.1021/jo200600n

  日期：2011.6.17

  The SmI2-mediated radical coupling reactions of beta-hydroxylated pyrrolidine/piperidine aza-hemiacetals 8 and 9 and N,S-acetals 6 and 33 with alpha/beta-unsaturated compounds are described. This method allows a rapid access to beta-hydroxylated pyrrolidines, piperidines, pyrrolizidinones, and indolizidinones. Starting from N,S-acetal 33 and via a common intermediate 27, the alkaloids hyacinthacine A(2) (2), uniflorine A (3, 6-epi-casuarine), and the unnatural epimer 7-epi-casuarine (37) have been synthesized in four and five steps with overall yields of 34%, 16%, and 13%, respectively. The radical mechanism of the coupling reactions has been confirmed by controlled experiments, which also allowed deducing the anionic mechanism in the coupling between N,S-acetal 6 and carbonyl compounds. This demonstrates that the mechanisms of these SmI2-mediated reactions are switchable from Barbier-type anionic to radical by cooperative action of BF3 center dot OEt2 and t-BuOH.
• Total Synthesis of (−)-Uniflorine A
  作者：Camilla Parmeggiani、Daniele Martella、Francesca Cardona、Andrea Goti

  DOI：10.1021/np900435d

  日期：2009.11.30

  Total synthesis of (-)-uniflorine A (3) has been accomplished in nine steps and 11% overall yield from carbohydrate-based nitrone 5. The key steps of the synthetic strategy were a high regio- and complete stereoselective 1,3-dipolar cycloaddition of alkene 6 with nitrone 5, a Tamao-Fleming reaction for replacing the silicon substituent with a hydroxy group with retention of configuration, and a Mitsunobu reaction to establish the correct configuration of the target molecule at C-6.
• Stereocomplementary synthesis of casuarine and its 6-<i>epi</i>-, 7-<i>epi</i>-, and 6,7-di<i>epi</i>-stereoisomers
  作者：Yi-Xian Li、Jun-Zhe Wang、Atsushi Kato、Yuna Shimadate、Maki Kise、Yue-Mei Jia、George W. J. Fleet、Chu-Yi Yu

  DOI：10.1039/d1ob01725j

  日期：——

  A stereocomplementary strategy allows the efficient synthesis of casuarine, 6-epi-casuarine, 7-epi-casuarine, and 6,7-diepi-casuarine from a cyclic nitrone and a nitrone-derived aldehyde. Their glycosidase inhibition profiles were compared.

  立体互补策略可实现从环状亚硝基化合物和亚硝基化合物衍生的醛中高效合成卡苏林、6-epi-卡苏林、7-epi-卡苏林和6,7-二epi-卡苏林。它们的糖苷酶抑制剖面进行了比较。