Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition

Hagihara Shuichi; Hanaya Kengo; Sugai Takeshi; Shoji Mitsuru

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Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition

机译：使用Regio-and Dia对映选择性的Englerin合成[4 + 3]环加成

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Englerin A, a guaiane sesquiterpene isolated from Phyllanthus engleri, showed highly potent and selective growth inhibitory activities against renal cancer cell lines. We synthesized the key tricyclic intermediate from commercially available 2,2-dimethyl- 1,3-dioxan-5-one via regio- and diastereoselective [4+3] cycloaddition between the formyl enol silyl ether and the disubstituted furan, in 4.8% total yield over 10 steps.

机译：叶下珠素A是从叶下珠中分离得到的一种愈创木烯倍半萜，对肾癌细胞系具有很强的选择性生长抑制活性。我们以市售的2,2-二甲基-1,3-二氧六环-5-酮为原料，通过甲酰基烯醇硅醚和二取代呋喃之间的区域选择性和非对映选择性[4+3]环加成反应合成了关键的三环中间体，10步总收率为4.8%。

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《The Journal of Antibiotics: An International Journal》 |2018年第2期|共6页
作者
Hagihara Shuichi; Hanaya Kengo; Sugai Takeshi; Shoji Mitsuru;
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作者单位

Keio Univ Dept Pharmaceut Sci Fac Pharm Tokyo Japan;

Keio Univ Dept Pharmaceut Sci Fac Pharm Tokyo Japan;

Keio Univ Dept Pharmaceut Sci Fac Pharm Tokyo Japan;

Keio Univ Dept Pharmaceut Sci Fac Pharm Tokyo Japan;

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正文语种 eng
中图分类药学;
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3. Diastereoselective Synthesis of 1,10-Dihydropyrrolo 1,2-a 1,10phenanthroline Derivatives via 1,3-Dipolar Cycloaddition Reaction [J] . LIU Zhen-ming, FANG Jun, YAN Chao-guo 高等学校化学研究（英文版） . 2013,第006期
4. Highly Concise Synthesis of 3'-"Up"-ethynyl-5'-methylbicyclo-[3.1.0]-hexyl Purine and Pyrimidine Nucleoside Derivatives Using Rhodium(II) Carbenoid Cycloaddition and Highly Diastereoselective Grignard Reaction [J] . YANG Zunhua, JEONG Lak Shin, MOON Hyung Ryong, 中国化学（英文版） . 2009,第012期
5. Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition [J] . Hagihara Shuichi, Hanaya Kengo, Sugai Takeshi, The Journal of Antibiotics: An International Journal . 2018,第2期

机译：使用Regio-and Dia对映选择性的Englerin合成[4 + 3]环加成
6. Erratum:Concise Formal Synthesis of (+)-Englerin A and Total Synthesis of (-)-Orientalol F: Establishment of the Stereochemistry of the Organocatalytic [4+3]-Cycloaddition Reaction [J] . Chao-Lei Wang, Bing-Feng Sun, Shu-Guang Chen, Synlett . 2012,第8期

机译：勘误：（+）-烯丙基甲醚的简明形式合成和（-）-东方醇F的全合成：有机催化[4 + 3]-环加成反应的立体化学的建立
7. Concise Formal Synthesis of (+)-Englerin A and Total Synthesis of (-)- Orientalol F: Establishment of the Stereochemistry of the Organocatalytic [4+3]-Cycloaddition Reaction [J] . Chao-Lei Wang, Bing-Feng Sun, Shu-Guang Chen, Synlett . 2012,第2期

机译：简明形式的（+）-Englerin A的合成和（-）-Orientalol F的全合成：有机催化[4 + 3]-环加成反应的立体化学的建立。
8. Regio- and Diastereoselective Photodimerization Reactions of Chiral Coumarin-3-Carboxamides [C] . Kennosuke Itoh, Fumiya Odate, Takuma Karikomi 日本化学会春季年会講演予稿集 . 2018

机译：手性香豆素-3-甲酰胺的测度和非对映选择性光电二聚体化反应
9. Development and application of a highly diastereoselective formal [3+3] cycloaddition reaction for the synthesis of heterocyclic natural products. [D] . McLaughlin, Michael Jeffrey. 2002

机译：高度天然的非对映选择性形式[3 + 3]环加成反应的开发和应用，用于合成杂环天然产物。
10. Enantioselective Formal Synthesis of (−)-Englerin A via a Rh-catalyzed 4+3 Cycloaddition Reaction [O] . Jing Xu, Eduardo J.E. Caro-Diaz, Emmanuel A. Theodorakis -1

机译：通过铑催化的4 + 3环加成反应Englerin a - （ - ）对映选择性合成的正式
11. Generation of cationic 2-azabutadienes from N,S-acetals and their use for the regio- and diastereoselective synthesis of 1,2,3,4-tetrahydroquinolines by intermolecular [4p+ + 2p] cycloadditions [O] . Uwe Beifuss, Sabine Ledderhose, Vladimir Ondrus 2005

机译：从N，s-缩醛生成阳离子2-氮杂丁二烯及其用于通过分子间[4p + + 2p]环加成的区域和非对映选择性合成1,2,3,4-四氢喹啉的用途
12. Enantiomerically Pure Acetals in Organic Synthesis: Resolutions and Diastereoselective Alkylations of Alpha-Hydroxy Esters. [R] . Fryling, J. A. 1990

机译：有机合成中的对映体纯的缩醛：α-羟基酯的分辨率和非对映选择性烷基化。

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Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition

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