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Literature DB >> 28765590

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

Shuichi Hagihara¹, Kengo Hanaya¹, Takeshi Sugai¹, Mitsuru Shoji¹.

Abstract

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.

Entities: Chemical Disease Species

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Year: 2017 PMID： 28765590 DOI： 10.1038/ja.2017.91

Source DB: PubMed Journal: J Antibiot (Tokyo) ISSN： 0021-8820 Impact factor: 2.649

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References

18 in total

1. Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition.

Authors: Taiki Hanari; Naoyuki Shimada; Yasunobu Kurosaki; Neetipalli Thrimurtulu; Hisanori Nambu; Masahiro Anada; Shunichi Hashimoto
Journal: Chemistry Date: 2015-07-15 Impact factor: 5.236

2. A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure.

Authors: Kohei Yamada; Hikaru Fujita; Munetaka Kunishima
Journal: Org Lett Date: 2012-09-20 Impact factor: 6.005

3. Stereocontrolled total synthesis of (-)-englerin A.

Authors: Keisuke Takahashi; Keita Komine; Yuichi Yokoi; Jun Ishihara; Susumi Hatakeyama
Journal: J Org Chem Date: 2012-08-17 Impact factor: 4.354

4. Collective total synthesis of englerin A and B, orientalol E and F, and oxyphyllol: application of the organocatalytic [4+3] cycloaddition reaction.

Authors: Jie Wang; Shu-Guang Chen; Bing-Feng Sun; Guo-Qiang Lin; Yong-Jia Shang
Journal: Chemistry Date: 2013-01-04 Impact factor: 5.236

5. Total Synthesis of (±)-Englerin A Using An Intermolecular [3+2] Cycloaddition Reaction of Platinum-Containing Carbonyl Ylide.

Authors: Hiroyuki Kusama; Aoi Tazawa; Kento Ishida; Nobuharu Iwasawa
Journal: Chem Asian J Date: 2015-10-08

6. Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-Alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful reactants for Lewis acid catalyzed [4 + 3] cyclizations.

Authors: R A Aungst; R L Funk
Journal: Org Lett Date: 2001-11-01 Impact factor: 6.005

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

1. Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition.

2. A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure.

3. Stereocontrolled total synthesis of (-)-englerin A.

4. Collective total synthesis of englerin A and B, orientalol E and F, and oxyphyllol: application of the organocatalytic [4+3] cycloaddition reaction.

5. Total Synthesis of (±)-Englerin A Using An Intermolecular [3+2] Cycloaddition Reaction of Platinum-Containing Carbonyl Ylide.

6. Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-Alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful reactants for Lewis acid catalyzed [4 + 3] cyclizations.

7. Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction.

8. Englerin A, a selective inhibitor of renal cancer cell growth, from Phyllanthus engleri.

9. A formal synthesis of (-)-englerin A by relay ring closing metathesis and transannular etherification.

10. Total synthesis of englerin A.